Ethyl Acetate → HCID 86594408, compound

HRID 1816447Notes

Reaction equation

HRID 1816447 reaction equation
[CH2:1]([O:3][CH:4]([S:29][CH2:30][CH3:31])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:28])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23]Br)=[CH:13][C:12]=1[N+:25]([O-:27])=[O:26])[CH3:2].[OH:32][C:33]1[C:47]([O:48][CH3:49])=[CH:46][C:36]2[C:37](=[O:45])[N:38]3[CH2:44][CH2:43][CH2:42][C@H:39]3[CH2:40][NH:41][C:35]=2[CH:34]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC(C)=O.O>[CH2:1]([O:3][CH:4]([S:29][CH2:30][CH3:31])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:28])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][O:32][C:33]2[C:47]([O:48][CH3:49])=[CH:46][C:36]3[C:37](=[O:45])[N:38]4[CH2:44][CH2:43][CH2:42][C@H:39]4[CH2:40][NH:41][C:35]=3[CH:34]=2)=[CH:13][C:12]=1[N+:25]([O-:27])=[O:26])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10944782HCID 10944782, compoundHCID 67282738HCID 67282738, compound

Product 1

HCID 86594408HCID 86594408, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (2S)-N-[4-(4-bromobutoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal of formula I (535 mg, 1 mmol), 8-hydroxy-7-methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrol[2,1-c][1,4]benzodiazepine-5-one (248 mg, 1 mmol) of the formula II and K2CO3 (414 mg, 3 mmol) in dry acetone (20 mL) was refluxed for 48 h. After the completion of reaction as indicated by TLC, EtOAc, the reaction mixture was poured on to the water and then extracted with ethylacetate. Evaporation of the organic layer gave the crude product, which was further purified by column chromatography on silica gel eluting with EtOAc:hexane (8:2) gave the pure (2S)-N-{4-[4-(7-Methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy)butoxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal III.

Workup

  1. customAfter the completion of reaction
  2. extractionextracted with ethylacetate
  3. customEvaporation of the organic layer
  4. customgave the crude product, which
  5. customwas further purified by column chromatography on silica gel eluting with EtOAc:hexane (8:2)

Sources & evidence

ORD record
ord-955f9b75d1ca47be9f9cee34bb9fe115
Source dataset
uspto-grants-2005_04
Patent number
US06884799B2

Reaction notes

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