HCID 22106927, compound → HCID 57310336, compound

HRID 1456578Notes

Reaction equation

HRID 1456578 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([OH:9])[CH:8]=1.CC(C)([O-])C.[K+].Cl[CH2:25][CH2:26][C@@H:27]1[CH2:31][C@@H:30]([O:32][C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[CH2:29][N:28]1[C:38]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:39]>CN(C)C(=O)C>[CH3:35][N:34]([CH3:36])[C:33]([O:32][C@H:30]1[CH2:29][N:28]([C:38]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:39])[C@H:27]([CH2:26][CH2:25][O:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:31]1)=[O:37]

Participants

5

Reactant 3

HCID 22106927HCID 22106927, compoundHCID 23665647Potassium tert-butoxideHCID 57115324HCID 57115324, compound

Product 1

HCID 57310336HCID 57310336, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

670 mg of 5-methoxy-2-(2-phenylethyl)phenol (prepared as described in Preparation 1) were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 360 mg of potassium t-butoxide and 1000 mg of (2S,4R)-2-(2-chloroethyl)-4-dimethylcarbamoyloxy-1-octyloxycarbonylpyrrolidine and extracted in the same manner as described in step (a) of Example 2. The resulting oily substance was purified by silica gel column chromatography, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1500 mg (yield 99%) of the title compound as an oily substance.

Workup

  1. extractionextracted in the same manner
  2. customThe resulting oily substance was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c491c3dd3acb4c70a6460a4f770e3d3a
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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