Water → HCID 57656171, compound

HRID 911406Notes

Reaction equation

HRID 911406 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([N:20]=[CH:21][C:22]3[S:26][CH:25]=[N:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:20][CH2:21][C:22]3[S:26][CH:25]=[N:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57655927HCID 57655927, compound

Product 1

HCID 57656171HCID 57656171, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-(t-butoxycarbonyl)-7-chloro-6-(thiazol-5-ylmethyleneamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (228 mg, 0.58 mmol) in methanol (10 mL), add sodium borohydride (263 mg, 7 mmol) and reflux for 28 h. Cool to ambient temperature, dilute with EtOAc and add slowly water. Separate the organic layer, extract the aqueous layer three times with EtOAc. Combine the organic extracts, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:3) to give the desired intermediate as a colorless oil (134 mg, 58%). MS (ES+) m/z: 394 (M+H)+.

Workup

  1. temperaturereflux for 28 h
  2. customSeparate the organic layer
  3. extractionextract the aqueous layer three times with EtOAc
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-49eeeeb939aa4710af11a23cb0732d7f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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