Ethyl Acetate → (2,2,2-Trifluoro-ethyl)-carbamic acid (S)-1-[(S)-5-(2-hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester

HRID 31037Notes

Reaction equation

HRID 31037 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C@@H:16]([NH:19][C:20]([C@@H:22]([O:24][C:25](=[O:32])[NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH3:23])=[O:21])[C:15]2[CH:33]=[CH:34][CH:35]=[CH:36][C:14]=2[C:13]2[CH:37]=[CH:38][CH:39]=[CH:40][C:12]1=2)C1C=CC=CC=1.C(OCC)(=O)C>CCCCCCC>[OH:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C@@H:16]([NH:19][C:20]([C@@H:22]([O:24][C:25](=[O:32])[NH:26][CH2:27][C:28]([F:29])([F:30])[F:31])[CH3:23])=[O:21])[C:15]2[CH:33]=[CH:34][CH:35]=[CH:36][C:14]=2[C:13]2[CH:37]=[CH:38][CH:39]=[CH:40][C:12]1=2

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 58972461(2,2,2-Trifluoro-ethyl)-carbamic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester

Product 1

HCID 24875582(2,2,2-Trifluoro-ethyl)-carbamic acid (S)-1-[(S)-5-(2-hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Using (2,2,2-trifluoro-ethyl)-carbamic acid (S)-1-[(S)-5-(2-benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl]-ethyl ester, the title compound was prepared in the same manner as example 3. Final chromatography (silica, gradient of ethyl acetate in heptane 5-90%) afforded the title compound as white solid (70%). MS: m/e=466(M+H+).

Workup

  1. customthe title compound was prepared in the same manner as example 3

Sources & evidence

ORD record
ord-c10a847e3ead442a816b854067f3575f
Source dataset
uspto-grants-2008_09
Patent number
US07425551B2

Reaction notes

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