tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(3-ethoxy-3-oxopropyl)-1,4-oxazepane-4-carboxylate

HRID 1022673Notes

Reaction equation

HRID 1022673 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8]>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11][C@H:10]2[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 66976531tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975164tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-(3-ethoxy-3-oxopropyl)-1,4-oxazepane-4-carboxylateYield 112.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a solution (1.1 mL) of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate (100 mg) in methanol was added, under a nitrogen atmosphere, 3% platinum/activated carbon (23 mg), and the mixture was stirred under a hydrogen atmosphere for 1 hr. The reaction mixture was filtered through celite, and concentrated under reduced pressure to give the title compound (113 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-128f9d83102d4add8bb69ed54137ed10
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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