Potassium Hydroxide → HCID 58495474, compound

HRID 1191143Notes

Reaction equation

HRID 1191143 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:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>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:43])[C:39]([CH3:42])([CH3:41])[CH3:40])=[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])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21642BromopinacoloneHCID 58495472HCID 58495472, compound

Product 1

HCID 58495474HCID 58495474, compoundYield 30%

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 (57 mg, 0.1 mmol) in methanol (5 mL). Add potassium hydroxide (65 mg, 1.1 mmol) and heat the mixture for 3 h at 65° C. Then add 1-bromo-3,3-dimethyl-2-butanone and heat at 65° C. for 2 h. Cool the mixture 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/diethyl ether (7:3) to obtain the desired intermediate as an oil (18 mg, 30%).

Workup

  1. temperatureCool the mixture
  2. washWash the organic phase with water
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/diethyl ether (7:3)

Sources & evidence

ORD record
ord-97cadbf691c44a24b360b8ea9ba2ee57
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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