Potassium Hydroxide → HCID 58495581, compound

HRID 1191145Notes

Reaction equation

HRID 1191145 reaction equation
[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[CH:27]=[CH:26][C:25]([S:28]C(=O)N(C)C)=[CH: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].[OH-].[K+].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39]>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[CH:27]=[CH:26][C:25]([S:28][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH: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]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 60984Methyl bromoacetateHCID 58495472HCID 58495472, compound

Product 1

HCID 58495581HCID 58495581, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-(tert-butoxycarbonyl)-7-chloro-6-(4-dimethylcarbamoylthio-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (270 mg, 0.5 mmol) in methanol (20 mL). Add potassium hydroxide (308 mg, 5.5 mmol) and heat the mixture for 3 h at 65° C. Add methyl bromoacetate (0.52 mL, 5.5 mmol) and heat at 65° C. for 3 h. Cool the mixture to room temperature and dilute with EtOAc. Wash the organic phase with water, dry over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate as an oil (203 mg, 75%).

Workup

  1. washWash the organic phase with water
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-9dc63bae1065441d9c9b9e2d084c2c13
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…