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 626629Notes

Reaction equation

HRID 626629 reaction equation
[CH:1]1[C:13]2[CH:12]([O:14][C:15](=[O:46])[N:16]([CH3:45])[C@@H:17]([C:29](=[O:44])[NH:30][C@H:31]([CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]C=C)[CH:32]([CH3:34])[CH3:33])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]=[CH2:28])=[CH:21][CH:20]=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]([O:14][C:15](=[O:46])[N:16]([CH3:45])[C@@H:17]3[CH2:18][C:19]4=[CH:20][CH:21]=[C:22]([CH:23]=[CH:24]4)[O:25][CH2:26][CH:27]=[CH:28][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][O:36][CH2:35][C@H:31]([CH:32]([CH3:34])[CH3:33])[NH:30][C:29]3=[O:44])[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 867279399H-fluoren-9-yl-methyl[(R)-2-(4-allyloxyphenyl)-1-((S)-1-hept-6-enyloxymethyl-2-methylpropylcarbamoyl)ethyl]carbamate

Product 1

HCID 867279389H-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 90.6%

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-812eb20725b8419fabbcc6e663748349
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Reaction notes

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