Hydrochloric Acid → HCID 46899290, compound

HRID 602799Notes

Reaction equation

HRID 602799 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:15]([S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Br:39])[CH:34]=3)(=[O:32])=[O:31])([CH:17]3[CH2:29][C:20]4[NH:21][C:22]5[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][C:27]=5[C:19]=4[CH2:18]3)[F:16])=[N:13][N:14]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>C1COCC1>[Br:39][C:35]1[CH:34]=[C:33]([S:30]([C:15]([CH:17]2[CH2:29][C:20]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][C:27]=4[C:19]=3[CH2:18]2)([F:16])[C:12]2[O:11][C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:40])=[O:2])=[CH:9][CH:8]=3)=[N:14][N:13]=2)(=[O:32])=[O:31])[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46899291HCID 46899291, compound

Product 1

HCID 46899290HCID 46899290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 13 mg (0.02 mmol) of (RS, SR) 4-{5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid methyl ester in a 1:1 mixture of 0.5 mL of THF and 0.5 mL of 1M aqueous LiOH was stirred at RT during one hour. Diluted aqueous HCl was added and the mixture extracted twice with dichloromethane. Drying of the combined organic phases over Na2SO4, filtration and evaporation of the solvent gave ca 13 mg (quantitative) of (RS, SR) 4-{5-[(3-bromo-benzenesulfonyl)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,3,4]oxadiazol-2-yl}-benzoic acid as a yellow solid, MS: 632 (MH30 , 1Br).

Workup

  1. extractionthe mixture extracted twice with dichloromethane
  2. dry with materialDrying of the combined organic phases over Na2SO4, filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-9375bc26dc674908ab948c1c4e9bd111
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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