9H-fluoren-9-ylmethyl [(R)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)-2-(4-allyloxyphenyl)ethyl]carbamate → 9H-Fluoren-9-ylmethyl ((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)carbamate

HRID 2039998Notes

Reaction equation

HRID 2039998 reaction equation
[CH2:1]([O:4][CH2:5][C@@H:6]([NH:10][C:11]([C@H:13]([NH:25][C:26](=[O:42])[O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22]C=C)=[CH:17][CH:16]=1)=[O:12])[CH:7]([CH3:9])[CH3:8])[CH:2]=[CH2:3]>ClCCl>[CH:7]([C@@H:6]1[NH:10][C:11](=[O:12])[C@H:13]([NH:25][C:26](=[O:42])[O:27][CH2:28][CH:29]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=3[C:36]3[C:41]2=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:14][C:15]2=[CH:16][CH:17]=[C:18]([CH:19]=[CH:20]2)[O:21][CH2:22][CH:3]=[CH:2][CH2:1][O:4][CH2:5]1)([CH3:9])[CH3:8]

Participants

3

Reactant 1

HCID 683028399H-fluoren-9-ylmethyl [(R)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)-2-(4-allyloxyphenyl)ethyl]carbamate

Product 1

HCID 683028049H-Fluoren-9-ylmethyl ((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)carbamateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.25 g (2.20 mmol) of 9H-fluoren-9-ylmethyl [(R)-1-((S)-1-allyloxymethyl-2-methylpropylcarbamoyl)-2-(4-allyloxyphenyl)ethyl]carbamate and 0.40 g (0.659 mmol) of dichloro(o-isopropoxyphenylmethylene)(tricyclohexylphosphine)ruthenium (Hoyveda-Grubbs catalyst) in 610 ml of dichloromethane was stirred at 40° C. for 24 h. The reaction mixture was then concentrated, and the residue was purified by chromatography on silica gel. 1.03 g of the desired compound were obtained as a colorless solid.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-450fe069fb714ed586cd3711ea13196a
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

Loading…