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 1022992Notes

Reaction equation

HRID 1022992 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:42])[NH:17][C@@H:18]([C:30](=[O:41])[NH:31][C@H:32]([CH2:36][O:37][CH2:38][CH:39]=C)[CH:33]([CH3:35])[CH3:34])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]=C)=[CH:22][CH:21]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>ClCCl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:42])[NH:17][C@@H:18]3[CH2:19][C:20]4=[CH:21][CH:22]=[C:23]([CH:24]=[CH:25]4)[O:26][CH2:27][CH:28]=[CH:39][CH2:38][O:37][CH2:36][C@H:32]([CH:33]([CH3:35])[CH3:34])[NH:31][C:30]3=[O:41])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

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-42b2120f79d34da19700a9b52e032fd7
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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