4-Bromo-1,1,1-trifluorobutane → HCID 22392982, compound

HRID 1635022Notes

Reaction equation

HRID 1635022 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[NH:14][C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[F:36][C:37]([F:43])([F:42])[CH2:38][CH2:39][CH2:40]Br>CN(C=O)C.O.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH2:40][CH2:39][CH2:38][C:37]([F:43])([F:42])[F:36])[C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22392982HCID 22392982, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(benzoxycarbonyl)amino-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (3.7 g, 9.61 mmol) in 40 mL of anhydrous DMF at 0° C. was added potassium tert-butoxide (1.6 g, 14.4 mmol) in one portion. The reaction mixture was stirred 20 m. and 4,4,4-trifluoro-1-bromobutane (Lancaster; Windham, N.H.; 2.6 g, 13.4 mmol) was added. The reaction mixture was warmed to room temperature over 30 min. and the n diluted with 100 mL of water and 200 mL of methylene chloride. The layers were separated. The organic layer was extracted with water and dried over sodium sulfate. Purification of the crude product by silica gel column chromatography (0-3% ethyl acetate/methylene chloride) gave 1.52 g (32%) of an off white foam.

Workup

  1. customThe layers were separated
  2. extractionThe organic layer was extracted with water
  3. dry with materialdried over sodium sulfate
  4. customPurification of the crude product by silica gel column chromatography (0-3% ethyl acetate/methylene chloride)
  5. customgave 1.52 g (32%) of an off white foam

Sources & evidence

ORD record
ord-1a3670bed14a4ae69d6ef2a948be86f7
Source dataset
uspto-grants-2003_01
Patent number
US06509331B1

Reaction notes

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