Benzyl chloroformate → HCID 67491111, compound

HRID 1917411Notes

Reaction equation

HRID 1917411 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([O:16][C:17]([NH:19][C@@:20]12[CH2:27][C:26](=[CH2:28])[CH2:25][C@@H:24]1[CH2:23][N:22]([C@@H](C1C=CC=CC=1)C)[CH2:21]2)=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[CH2:5]([O:4][C:2]([N:22]1[CH2:23][C@@H:24]2[C@@:20]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])([CH2:27][C:26](=[CH2:28])[CH2:25]2)[CH2:21]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 67490871HCID 67490871, compound

Product 1

HCID 67491111HCID 67491111, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Benzyl chloroformate (0.250 ml, 1.75 mmol) was added to a solution of the residue containing (1S,5R)-1-tert-butoxycarbonylamino-7-methylene-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane (200 mg, equivalent to 0.437 mmol) in dichloromethane (1.94 ml) in a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 hours and at 40° C. for four hours. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→87:13→86:14→83:17→80:20→75:25) to give 95.1 mg of the title compound as a transparent oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→87:13→86:14→83:17→80:20→75:25)

Sources & evidence

ORD record
ord-bc2d0f3fb5924f7f80ff7aee0e1bf386
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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