Benzoyl isothiocyanate → (S)-Methyl 3-(3-benzoylthioureido)-2-(tert-butoxycarbonylamino)propanoate

HRID 1755487Notes

Reaction equation

HRID 1755487 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:16]([NH:24][C:25](=[S:26])[NH:1][CH2:2][C@H:3]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]([O:6][CH3:7])=[O:5])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 11746086(S)-Methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate

Product 1

HCID 86700130(S)-Methyl 3-(3-benzoylthioureido)-2-(tert-butoxycarbonylamino)propanoateYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of (S)-methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate (see US2007/93414A1, 10.3 g, 47.2 mmol) in anhydrous dichloromethane (170 mL) is slowly added benzoyl isothiocyanate (6.35 mL, 47.2 mmol). The reaction is stirred for 2.5 h while slowly warming to room temp. The solvent is removed in vacuo and the residue is purified by BIOTAGE® Silica gel chromatography on a 300 g Thompson Single Step silica cartridge using a linear gradient from 100% hexanes to 100% EtOAc over 10 column volumes to give 4.7 g (26.1%) of the title compound as a pale yellow solid. LC/MS (Condition A): ret. T=3.48 min, (M+Na) 404.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by BIOTAGE® Silica gel chromatography on a 300 g Thompson Single Step silica cartridge

Sources & evidence

ORD record
ord-e75d249543804f9ba70bafe14fcccf42
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

Loading…