(S)-4-hydroxy-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid methyl ester → (S)-4-Oxo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid methyl ester

HRID 1096205Notes

Reaction equation

HRID 1096205 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([N:8]1[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH2:10][CH2:9]1)[CH2:5][CH2:6][OH:7].O=C1[C@@H](N2C(=O)CCN(C3C=CC=C(C(F)(F)F)C=3)CC2)CCO1>>[CH3:1][O:2][C:3](=[O:26])[C@@H:4]([N:8]1[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH2:10][CH2:9]1)[CH2:5][CH:6]=[O:7]

Participants

3

Reactant 2

HCID 66783353(S)-4-hydroxy-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid methyl esterHCID 66783577HCID 66783577, compound

Product 1

HCID 86638381(S)-4-Oxo-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid methyl esterYield 97%

Procedure

In analogy to the procedure described in example 1I, (S)-4-hydroxy-2-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid methyl ester gave a mixture of 4-((S)-2-oxo-tetrahydro-furan-3-yl)-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one (ca 5-10%) and the title compound in 97% yield as orange oil. MS: 373.1 (MH+).

Workup

  1. customgave

Sources & evidence

ORD record
ord-17bfef3955e848fbbd8b18b7f35a6e47
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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