HCID 86756874, compound → HCID 86756873, compound

HRID 1979189Notes

Reaction equation

HRID 1979189 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:57][CH:58]([CH3:60])[CH3:59])[C:22]([NH:24][N:25]([CH2:53][CH:54]([CH3:56])[CH3:55])[C:26](=[O:52])[C@@H:27]([CH2:46][O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[NH:28]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>ClCCl.N1CCCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:57][CH:58]([CH3:60])[CH3:59])[C:22]([NH:24][N:25]([CH2:53][CH:54]([CH3:55])[CH3:56])[C:26](=[O:52])[C@@H:27]([CH2:46][O:47][C:48]([CH3:49])([CH3:51])[CH3:50])[NH2:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 1

HCID 86756874HCID 86756874, compound

Product 1

HCID 86756873HCID 86756873, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

A solution of 0.86 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-[N-(9-fluorenylmethyloxycarbonyl)-O-tert.butyl-D-seryl]-4-methylvalerohydrazide in a mixture of 8 ml of dichloromethane and 2 ml of piperidine was stirred at room temperature for 3 hours. The solution was evaporated and the residue was treated with diethyl ether. The ethereal solution was filtered and evaporated. Chromatography on silica gel using methanol/dichloromethane (1:19) for the elution followed by evaporation gave 0.39 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-2′-(O-tert.butyl-D-seryl)-4-methylvalerohydrazide in the form of a gum.

Workup

  1. customThe solution was evaporated
  2. additionthe residue was treated with diethyl ether
  3. filtrationThe ethereal solution was filtered
  4. customevaporated
  5. washfor the elution
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-4830cbf59b8d4f5383b91c85c0a5f94c
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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