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472654

Sigma-Aldrich

N-Boc-2-aminoacetaldehyde

95%

Synonym(s):

tert-Butyl N-(2-oxoethyl)carbamate

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1 G
$102.00
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$250.00
25 G
$720.00

About This Item

Linear Formula:
HCOCH2NHCO2C(CH3)3
CAS Number:
89711-08-0
Molecular Weight:
159.18
MDL number:
MFCD01321273
UNSPSC Code:
12352100
PubChem Substance ID:
24870815
NACRES:
NA.22
assay:
95%

$102.00

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Quality Level

100

assay

95%

refractive index

n20/D 1.455 (lit.)

functional group

aldehyde
amine

storage temp.

−20°C

SMILES string

CC(C)(C)OC(=O)NCC=O

InChI

1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)

InChI key

ACNRTYKOPZDRCO-UHFFFAOYSA-N

Gene Information

human ... CTSK(1513)

General description

N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.[1]

Application

α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.[2]
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.[3]
N-Boc-2-aminoacetaldehyde may be employed in the following:
  • As a starting reagent in the total synthesis of (+)-negamycin.[4]
  • Synthesis of (E)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate.[5]
  • Synthesis of 2,2′-bipyridine.[6]
A building block in the synthesis of a protected pyrroloproline.[7]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3472
MKCQ7930
MKCR3358
MKCP6447
MKCN5788

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Yoshio Hayashi et al.
Chemical communications (Cambridge, England), (20)(20), 2379-2381 (2008-05-14)
Herein, we describe an efficient strategy for the total synthesis of (+)-negamycin using commercially available achiral N-Boc-2-aminoacetaldehyde as starting material with 42% overall yield for a limited number of steps.
Diethyl [3-Cyano-2-Oxo-3-(Triphenylphosphoranylidene) propyl] phosphonate: A Useful Horner-Wadsworth-Emmons Reagent for alpha-Keto (Cyanomethylene)-triphenylphosphoranes from Carbonyl Compounds.
Lee K.
Bull. Korean Chem. Soc., 28(10), 1641-1641 (2007)
Anniina Erkkilä et al.
The Journal of organic chemistry, 71(6), 2538-2541 (2006-03-11)
A rapid and extremely convenient method for alpha-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and
Anna Turetsky et al.
Scientific reports, 4, 4782-4782 (2014-04-25)
A number of Bruton's tyrosine kinase (BTK) inhibitors are currently in development, yet it has been difficult to visualize BTK expression and pharmacological inhibition in vivo in real time. We synthesized a fluorescent, irreversible BTK binder based on the drug
The Journal of Organic Chemistry, 70, 10869-10869 (2005)
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