(R)-N-(7-benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamide → (R)-N-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-hydroxy-acetamide

HRID 2355228Notes

Reaction equation

HRID 2355228 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH:21][C:22](=[O:32])[CH2:23][O:24]CC4C=CC=CC=4)[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH:21][C:22](=[O:32])[CH2:23][OH:24])[O:17]3)=[CH:12][CH:11]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 58869170(R)-N-(7-benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 16225763(R)-N-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-hydroxy-acetamideYield 23,518.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)—N-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamide (100 mg, 0.22 mmol) and Perlman's catalyst (12 mg) were added to 15 mL MeOH and hydrogenated for 18 hours at 1.5 atmospheres of hydrogen. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography to give 18.7 g of (R)—N-(7-Benzenesulfonyl-chroman-2-ylmethyl)-2-hydroxy-acetamide, MS (M+H)=362.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f305fc8ed78346a9aef351fe875f5d3f
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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