Sulfuric Acid → HCID 54290816, compound

HRID 1953231Notes

Reaction equation

HRID 1953231 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:27][C:28](=[CH2:30])[CH3:29].S(=O)(=O)(O)O>C(Cl)Cl>[C:28]([O:23][C:22]([C:17]1([NH:16][S:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][C:5]3[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)(=[O:14])=[O:15])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:24])([CH3:30])([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 18365441HCID 18365441, compound

Product 1

HCID 54290816HCID 54290816, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(4-fluoro-phenoxy) benzenesulfonylamino]-cyclopentanecarboxylic acid (10.22 g, 27 mmole) in 100 mL methylene chloride at -78□ C. was condensed 40 mL of isobutylene. Concentrated sulfuric acid (0.3 mL) was added and the mixture allowed to warm to ambient temperature and stirred for 22 hours. The mixture was then washed with 3×50 mL 2N NaOH and the organic layer dried over magnesium sulfate and evaporated to give 11.17 g (95%) of 1-[4-(4-fluoro-phenoxy)-benzenesulfonylamino]-cyclopentanecarboxylic acid tert-butyl ester. 1H NMR (CDCl3) □ 7.74-7.77 (m, 2H), 6.85-7.13 (m, 6H), 4.95 (s, 1H), 1.92-2.02 (m, 2H), 1.78-1.88 (m, 2H), 1.50-1.65 (m, 4H), 1.35 (s, 9H).

Workup

  1. washThe mixture was then washed with 3×50 mL 2N NaOH
  2. dry with materialthe organic layer dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1e14876ffd034d07b847b7b762158883
Source dataset
uspto-grants-2000_09
Patent number
US06114568

Reaction notes

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