Triethylamine → HCID 14421499, compound

HRID 1722354Notes

Reaction equation

HRID 1722354 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][CH:12]1[CH2:14][O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:30])[CH2:27][CH2:28][SH:29].C(N(CC)CC)C>CO>[CH2:1]([O:8][C:9]1[C:18]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][CH:12]([OH:13])[CH2:14][S:29][CH2:28][CH2:27][C:26]([O:25][CH3:24])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18050Methyl 3-mercaptopropionateHCID 14421498HCID 14421498, compound

Product 1

HCID 14421499HCID 14421499, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g (59 mmol) of (2-benzyloxy-3-cyclopentylbenzyl)-oxirane, 24.5 g (0.204 mol) of methyl-3-mercaptopropionate and 26.1 g (0.257 mol) of triethylamine are stirred in 150 ml of dry methanol at room temperature and under protective gas (argon or nitrogen) overnight. The solvent is removed by distillation in vacuo, and the residue is chromatographed on a silica gel column (gradient dichloromethane→ethyl acetate). 19.0 g (65% of theory) or methyl 7-(2-benzyloxy-3-cyclopentylphenyl)-6-hydroxy-4-thiaheptanoate are obtained.

Workup

  1. customThe solvent is removed by distillation in vacuo
  2. customthe residue is chromatographed on a silica gel column (gradient dichloromethane→ethyl acetate)

Sources & evidence

ORD record
ord-3b74e1bd0d14475ebec4864bcaae10a1
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

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