Benzyl chloroformate → HCID 67490811, compound

HRID 1917385Notes

Reaction equation

HRID 1917385 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[CH2:28][N:27]([C@@H](C3C=CC=CC=3)C)[CH2:26][C@@H:25]1[CH2:24][CH:23]=[CH:22][CH2:21]2)=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[CH2:5]([O:4][C:2]([N:27]1[CH2:28][C@@:20]2([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[C@@H:25]([CH2:24][CH:23]=[CH:22][CH2:21]2)[CH2:26]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 67491156HCID 67491156, compound

Product 1

HCID 67490811HCID 67490811, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (0.600 mL, 4.20 mmol) was added to a solution of (1S,6S)-1-tert-butoxycarbonylamino-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene (479 mg, 1.40 mmol) in dichloromethane (4.66 mL) in a nitrogen atmosphere, and the mixture was stirred at room temperature for 17 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→75:25→66:34) to give 401 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThen, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→95:5→90:10→75:25→66:34)

Sources & evidence

ORD record
ord-4c1806f5bc204320a0324dea4c03c1c2
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…