Dichloromethane → [(S)-2-Oxo-1-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

HRID 1372972Notes

Reaction equation

HRID 1372972 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O([CH2:29][C:30]([F:33])([F:32])[F:31])S(C(F)(F)F)(=O)=O.ClCCl>CO>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

Product 1

HCID 69039568[(S)-2-Oxo-1-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an analogous manner to that described in Example 25 a), the alkylation of the (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4] diazepin-3-yl)-carbamic acid tert-butyl ester with 2,2,2-trifluoroethyl triflate, yielded, after chromatography on silica gel using a 98:2-mixture of dichloromethane and methanol as the eluent, the title compound as a white solid;

Workup

  1. customyielded

Sources & evidence

ORD record
ord-7b9cf1ca0d374e839902b44777bc2b74
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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