N-(tert-butoxycarbonyl)glycine → ({[(4-Chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-carbamic acid tert-butyl ester

HRID 2425269Notes

Reaction equation

HRID 2425269 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[C:17]([O:21][C:22](=[O:23])[NH:24][CH2:25][C:26](=[O:27])[NH:16][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 162190964-Chlorobenzhydrylamine hydrochloride

Product 1

HCID 59689146({[(4-Chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-carbamic acid tert-butyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 7.9 mmol C-(4-chloro-phenyl)-C-phenyl-methylamine hydrochloride (CA [5267-39-0]) in 100 ml acetonitrile was treated successively with 7.9 mmol N-tert.butyloxycarbonyl glycine, 39 mmol DIPEA and 8.7 mmol TBTU. After stirring for 1 hour at room temperature, the mixture was concentrated. Chromatography (SiO2; ethyl acetate/cyclohexane) yielded the title compound as a colorless solid. Yield=84%.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-753e21f74ce84ee8b7762e65dc319521
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

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