Acetic Acid → Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate

HRID 1466011Notes

Reaction equation

HRID 1466011 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+].C(O)(=O)C>CO.CCOC(C)=O>[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

7

Reactant 4

HCID 176Acetic AcidHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 117599485tert-Butyl [2-(4-nitrophenyl)ethyl](2-oxoethyl)carbamate

Product 1

HCID 131732667Ethyl [(2-{(tert-butoxycarbonyl) [2-(4-nitrophenyl)ethyl]amino}ethyl)amino]acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-Butyl [2-(4-nitrophenyl)ethyl](2-oxoethyl)carbamate (0.95 g, 3.1 mmol) in MeOH (20 mL) was added ethyl aminoacetate hydrochloride (480 mg, 3.4 mmol), sodium cyanoborohydride (590 mg, 9.3 mmol) and a drop of acetic acid. The mixture was allowed to stir at RT for 16 hours. LC showed good reaction. The reaction was diluted with EtOAc, washed with aqueous sodium carbonate, dried over sodium sulfate, and purified by silica gel chromatography to furnish the title compound. LC-MS (IE, m/z): 393 [M+1]+.

Workup

  1. customreaction
  2. washwashed with aqueous sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3a6f7c6430cc488cb6ea9daba5c68ffe
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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