HCID 67317981, compound → HCID 59731913, compound

HRID 132166Notes

Reaction equation

HRID 132166 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[CH2:20][O:21][C:22](=[O:24])[CH3:23].[H][H]>CO>[CH3:1][O:2][C:3](=[O:33])[CH:4]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[CH2:20][O:21][C:22](=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 67317981HCID 67317981, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59731913HCID 59731913, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2-acetoxymethyl-4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-acrylic acid methyl ester (1.9 g, 4.2 mmol) in anhydrous methanol under nitrogen atmosphere was added 1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclootadiene)rhodium (I) trifluoromethanesulfonate (50 mg) and stirred on a Parr shaker at 50 psi of hydrogen atmosphere for 18 h. The solvent was evaporated and the desired product was crystallized from ethyl acetate-hexane in 90% yield. MS (ESI) 458 (M+H); Rf=1.81.

Workup

  1. customThe solvent was evaporated
  2. customthe desired product was crystallized from ethyl acetate-hexane in 90% yield

Sources & evidence

ORD record
ord-cea4a460961544bda988416ad7af7908
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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