(4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester → (4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid

HRID 1715834Notes

Reaction equation

HRID 1715834 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[CH:22][N:23]3[S:26]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[O:36][CH3:37])(=[O:28])=[O:27])=[CH:19][CH:18]=2)=[O:16])=[CH:10][CH:9]=1)(C)(C)C>Cl.O1CCOCC1>[Cl:35][C:33]1[CH:32]=[CH:31][C:30]([O:36][CH3:37])=[C:29]([S:26]([N:23]2[C:24]3[C:20](=[CH:19][CH:18]=[C:17]([C:15]([NH:14][C:11]4[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:38])=[O:5])=[CH:9][CH:10]=4)=[O:16])[CH:25]=3)[CH:21]=[CH:22]2)(=[O:28])=[O:27])[CH:34]=1

Participants

4

Reactant 1

HCID 68432753(4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester

Product 1

HCID 24962348(4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid tert-butyl ester (0.25 g, 0.46 mmol) was dissolved in 4M HCl in dioxane (4.00 mL) and stirred at room temperature for 18 hours. The volatiles were evaporated and the residue taken up in ethyl acetate/heptane 1:1 and sonicated. The solid was filtered washing with ethyl acetate/heptane 1:1 and dried under vacuum. (4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid was obtained as an off-white solid, 0.14 g (63%), MS (ISP): m/e=497.1 (M−H).

Workup

  1. customThe volatiles were evaporated
  2. customsonicated
  3. filtrationThe solid was filtered
  4. washwashing with ethyl acetate/heptane 1:1
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4a84fe0838614589b3cdbe857fff4172
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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