Boron tribromide → (S)-2-[4-(3,4-Dichloro-phenyl)-3-methyl-7-oxo-[1,4]diazepan-1-yl]-4-hydroxy-butyric Acid methyl ester

HRID 1096267Notes

Reaction equation

HRID 1096267 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH:17]([CH3:31])[CH2:16]1)[CH2:5][CH2:6][O:7]CC1C=CC=CC=1.B(Br)(Br)Br>>[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([N:15]1[C:21](=[O:22])[CH2:20][CH2:19][N:18]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH:17]([CH3:31])[CH2:16]1)[CH2:5][CH2:6][OH:7]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 66782967(S)-4-Benzyloxy-2-[4-(3,4-dichloro-phenyl)-3-methyl-7-oxo-[1,4]diazepan-1-yl]-butyric Acid methyl ester

Product 1

HCID 66782760(S)-2-[4-(3,4-Dichloro-phenyl)-3-methyl-7-oxo-[1,4]diazepan-1-yl]-4-hydroxy-butyric Acid methyl ester

Procedure

In analogy to the procedure described in example 1H, (S)-4-benzyloxy-2-[4-(3,4-dichloro-phenyl)-3-methyl-7-oxo-[1,4]diazepan-1-yl]-butyric acid methyl ester and boron tribromide (after warming up the reaction to maximum to −5° C.) gave after precipitation CH2Cl2/n-pentane 78% of the title compound as a 71:29 mixture of the (R) and (S) diastereomers. Off-white foam, MS: 447.0 (M+OAc−, 2Cl).

Workup

  1. temperatureafter warming up
  2. customthe reaction to maximum to −5° C.)
  3. customgave
  4. customafter precipitation CH2Cl2/n-pentane 78% of the title compound
  5. additionas a 71:29 mixture of the (R) and (S) diastereomers

Sources & evidence

ORD record
ord-80f5fded3052485382473b10cf4e040e
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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