HCID 22106941, compound → HCID 54165020, compound

HRID 1456587Notes

Reaction equation

HRID 1456587 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=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>[CH3:34][N:33]([CH3:35])[C:32]([O:31][C@H:29]1[CH2:28][N:27]([C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:38])[C@H:26]([CH2:25][CH2:24][O:8][C:7]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:30]1)=[O:36]

Participants

5

Reactant 3

HCID 22106941HCID 22106941, compoundHCID 23665647Potassium tert-butoxideHCID 57115324HCID 57115324, compound

Product 1

HCID 54165020HCID 54165020, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

520 mg of 6-fluoro-2-(2-phenylethyl)phenol (prepared as described in Preparation 10) were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 300 mg of potassium t-butoxide and 820 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 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 984 mg (yield 81 %) 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-32308484f9264da7b94c7d707ecb525b
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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