Glycine ethyl ester, hydrochloride → Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate

HRID 1466006Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:20][CH:21]=O)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[NH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:15]([O:14][C:13]([N:12]([CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:20][CH2:21][NH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:19])([CH3:16])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of tert-Butyl [2-(4-nitrophenyl)ethyl](2-oxoethyl)carbamate (0.52 g, 1.7 mmol) in MeOH (10 mL) was added ethyl aminoacetate hydrochloride (0.31 g, 2.2 mmol), sodium cyanoborohydride (1.1 g, 5.1 mmol), and a few drops of acetic acid. The mixture was allowed to stir at 25° C. for 16 hours. LC showed clean reaction. The product was purified by silica gel chromatography (Hexane:EtOAc) to deliver Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate. LC-MS (IE, m/z): 396 [M+1]+.

Workup

customreaction
customThe product was purified by silica gel chromatography (Hexane:EtOAc)

Sources & evidence

ORD record: ord-3b3bf2ce2bfa475bb0de61efb801260b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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