Sodium hydride → HCID 21138134, compound

HRID 1358884Notes

Reaction equation

HRID 1358884 reaction equation
[F:1][C:2]([F:44])([C:40]([F:43])([F:42])[F:41])[CH2:3][CH2:4][CH2:5][S:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:37][C@@:35]3([CH3:36])[C@@H:31]([CH2:32][CH2:33][C@@H:34]3[OH:38])[C@H:30]3[C@H:21]2[C:22]2[CH:23]=[CH:24][C:25]([OH:39])=[CH:26][C:27]=2[CH2:28][CH2:29]3)=[CH:16][CH:15]=1)=[O:7].[H-].[Na+].CC1C=CC(S(O[CH:58]2[CH2:62][CH2:61][CH2:60][CH2:59]2)(=O)=O)=CC=1.[Cl-].[NH4+]>CN(C)C=O>[CH:58]1([O:39][C:25]2[CH:24]=[CH:23][C:22]3[C@@H:21]4[C@H:30]([C@H:31]5[C@@:35]([CH2:37][C@@H:20]4[C:17]4[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][S:6]([CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:44])[C:40]([F:41])([F:42])[F:43])=[O:7])=[CH:19][CH:18]=4)([CH3:36])[C@@H:34]([OH:38])[CH2:33][CH2:32]5)[CH2:29][CH2:28][C:27]=3[CH:26]=2)[CH2:62][CH2:61][CH2:60][CH2:59]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonateHCID 88111276HCID 88111276, compound

Product 1

HCID 21138134HCID 21138134, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of the product prepared in Example 31, 8.7 cm3 of dimethylformamide and 82 mg of sodium hydride are agitated for 30 minutes. Then 486 mg of cyclopentyl 4-methylbenzenesulphonate is added, agitation is carried out for 5 hours, the whole is poured into an aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with salt water, dried and the solvent is evaporated off. The residue is chromatographed on silica (eluant: methylene chloride-isopropanol 95-5) and 861 mg of product is obtained which is crystallized from a methylene chloride/ethyl ether mixture and 777 mg of expected product is collected.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with salt water
  3. customdried
  4. customthe solvent is evaporated off
  5. customThe residue is chromatographed on silica (eluant: methylene chloride-isopropanol 95-5)

Sources & evidence

ORD record
ord-f8ebb8b9fe80406eaa0da6eed7af091b
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

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