9H-fluoren-9-yl-methyl [(R)-2-(4-allyloxyphenyl)-1-((S)-1-hept-6-enyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate → 9H-Fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamate

HRID 2040001Notes

Reaction equation

HRID 2040001 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@@H:12]([NH:29][C:30](=[O:46])[O:31][CH2:32][CH:33]2[C:45]3[CH:44]=[CH:43][CH:42]=CC=3C3[C:34]2=CC=CC=3)[C:13](=[O:28])[NH:14][C@H:15]([CH2:19][O:20][CH2:21]CCCCC=C)[CH:16]([CH3:18])[CH3:17])=[CH:7][CH:6]=1)C=C>ClCCl>[CH:16]([C@@H:15]1[NH:14][C:13](=[O:28])[C@H:12]([NH:29][C:30](=[O:46])[O:31][CH2:32][CH:33]2[C:34]3[CH:9]=[CH:10][CH:5]=[CH:6][C:7]=3[C:8]3[C:45]2=[CH:44][CH:43]=[CH:42][CH:11]=3)[CH2:11][C:8]2=[CH:9][CH:10]=[C:5]([CH:6]=[CH:7]2)[O:4][CH2:1][CH:32]=[CH:33][CH2:45][CH2:44][CH2:43][CH2:42][CH2:21][O:20][CH2:19]1)([CH3:17])[CH3:18]

Participants

3

Reactant 1

HCID 866559679H-fluoren-9-yl-methyl [(R)-2-(4-allyloxyphenyl)-1-((S)-1-hept-6-enyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

Product 1

HCID 866559669H-Fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamateYield 181.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.01 g (1.61 mmol) of 9H-fluoren-9-yl-methyl [(R)-2-(4-allyloxyphenyl)-1-((S)-1-hept-6-enyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate and 0.15 g (0.24 mmol) of dichloro(o-isopropoxyphenylmethylene)(tricyclohexylphosphine)ruthenium (Hoyveda-Grubbs catalyst) in 460 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. 0.87 g of the desired compound was 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-821da27b3aa64d20816e6d0b3717731c
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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