HCID 22106913, compound → HCID 53949785, compound

HRID 1456584Notes

Reaction equation

HRID 1456584 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([OH:8])[CH:7]=1.CC(C)([O-])C.[K+].Cl[CH2:24][CH2:25][C@@H:26]1[CH2:30][C@@H:29]([O:31][C:32](=[O:36])[N:33]([CH3:35])[CH3:34])[CH2:28][N:27]1[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:38]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:6]([CH:7]=1)[O:8][CH2:24][CH2:25][C@@H:26]1[CH2:30][C@@H:29]([O:31][C:32](=[O:36])[N:33]([CH3:35])[CH3:34])[CH2:28][N:27]1[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:38]

Participants

5

Reactant 3

HCID 22106913HCID 22106913, compoundHCID 23665647Potassium tert-butoxideHCID 57115324HCID 57115324, compound

Product 1

HCID 53949785HCID 53949785, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

680 mg of 5-chloro-2-(2-phenylethyl)phenol (prepared as described in Preparation 9) 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 1 .38 g (yield 91%) 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-1e4f5cf570e0413eb1c8db027f39e8a6
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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