HCID 59875793, compound → HCID 57224616, compound

HRID 1700974Notes

Reaction equation

HRID 1700974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:14]=[CH:15]/[CH2:16][C@@H:17]([C:26]([NH:28][C@H:29]([C:34]([NH:36][C@@H:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:38])=[O:35])[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:27])[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][CH2:16][C@@H:17]([C:26]([NH:28][C@H:29]([C:34]([NH:36][C@@H:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:38])=[O:35])[C:30]([CH3:31])([CH3:32])[CH3:33])=[O:27])[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 59875793HCID 59875793, compound

Product 1

HCID 57224616HCID 57224616, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of tert-butyl (3R,5E)-6-[3-chloro-(4-phenyl)phenyl]-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)hex-5-enoate (936 mg, 1.52 mmol) and p-toluenesulphonyl hydrazide (1.41 gm, 7.60 mmol) in toluene (15 mL) was stirred under nitrogen at reflux for 4 h. After being cooled, the mixture was diluted with ether (150 mL), and washed with water (50 mL), 0.5M hydrochloric acid (50 mL) and saturated aqueous sodium chloride (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate) to give tert-butyl (3R)-6-[3-chloro-(4-phenyl)phenyl]-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino)carbonyl)hexanoate (701 mg, 74%), as a colourless foam.

Workup

  1. temperatureat reflux for 4 h
  2. temperatureAfter being cooled
  3. washwashed with water (50 mL), 0.5M hydrochloric acid (50 mL) and saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dd49a712144443bdb60f04e284ff7c61
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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