(S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester → (S)-3-amino-5-benzoyl-1-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one

HRID 1374556Notes

Reaction equation

HRID 1374556 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9]1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 69508172(S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 69507477(S)-3-amino-5-benzoyl-1-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (260 mg, 0.66 mmol) was dissolved in a mixture of trifluoroacetic acid and dichloromethane (1:1, 2 ml) for 2.5 h. Upon evaporation of the volatile parts, (S)-3-amino-5-benzoyl-1-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one was obtained in sufficient purity for the next step.

Workup

  1. customUpon evaporation of the volatile parts

Sources & evidence

ORD record
ord-fc7b7bf14e0b43bc8ef030c6e043f9d5
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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