Hexane → 1-[[3-(Tert-butyl-dimethylsilanyloxy)propyl)-(4'-fluorobiphenyl-4-sulfonyl)amino]-cyclopentanecarboxylic acid benzyl ester

HRID 1872219Notes

Reaction equation

HRID 1872219 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:43]([Si:47]([O:50][CH2:51][CH2:52][CH2:53]I)([CH3:49])[CH3:48])([CH3:46])([CH3:45])[CH3:44].CCCCCC>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:53][CH2:52][CH2:51][O:50][Si:47]([C:43]([CH3:44])([CH3:46])[CH3:45])([CH3:48])[CH3:49])[S:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 11022956Tert-butyl-(3-iodopropoxy)-dimethylsilane2×HCID 154800081-(4'-Fluorobiphenyl-4-sulfonylamino)cyclopentanecarboxylic acid benzyl ester

Product 1

HCID 154800091-[[3-(Tert-butyl-dimethylsilanyloxy)propyl)-(4'-fluorobiphenyl-4-sulfonyl)amino]-cyclopentanecarboxylic acid benzyl esterYield 86.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4'-fluorobiphenyl-4-sulfonylamino)cyclopentanecarboxylic acid benzyl ester (23.0 grams, 50.7 mmol) in dry N,N-dimethylformamide (500 ml) at room temperature was added potassium hexamethyldisilazide (12.2 grams, 61.1 mmole) and, after 45 minutes, tert-butyl-(3-iodopropoxy)dimethylsilane (18.3 grams, 60.9 mmol). The resulting mixture was stirred at room temperature for 16 hours. Additional potassium hexamethyidisilazide (3.0 grams, 15 mmole) and tert-butyl-(3-iodopropoxy)-dimethylsilane (4.5 grams, 15 mmol) were then added. Stirring at room temperature was continued for a further 5 hours. The mixture was quenched by addition of saturated ammonium chloride solution. The N,N-dimethylformamide was removed by evaporation under vacuum. The residue was taken up in diethyl ether and washed successively with water, dilute aqueous hydrochloric acid solution and brine. After drying over magnesium sulfate, the diethyl ether was evaporated to afford a yellow oil. To this was added hexane and methylene chloride to induce crystallization of the starting material which was recovered by filtration. Evaporation of solvents from the filtrate afforded crude 1-[[3-(tert-butyl-dimethylsilanyloxy)propyl]-(4'-fluorobiphenyl-4-sulfonyl)amino]-cyclopentanecarboxylic acid benzyl ester as an amber oil (27.35 grams).

Workup

  1. stirringStirring at room temperature
  2. waitwas continued for a further 5 hours
  3. customThe mixture was quenched by addition of saturated ammonium chloride solution
  4. customThe N,N-dimethylformamide was removed by evaporation under vacuum
  5. washwashed successively with water, dilute aqueous hydrochloric acid solution and brine
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe diethyl ether was evaporated
  8. customto afford a yellow oil
  9. customcrystallization of the starting material which
  10. filtrationwas recovered by filtration
  11. customEvaporation of solvents from the filtrate

Sources & evidence

ORD record
ord-f4e62e42b00e4c6e928ec4f3150aa72d
Source dataset
uspto-grants-2000_08
Patent number
US06107337

Reaction notes

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