Hydrochloric Acid → HCID 58056569, compound

HRID 555671Notes

Reaction equation

HRID 555671 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[N:8]([S:16]([C:19]2[CH:20]=[N:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH:24]=2)(=[O:18])=[O:17])[CH:7]=1.[Li+].[OH-].CCCCCC.C(OCC)(=O)C.Cl>O1CCCC1>[Cl:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:16]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=3)[CH:24]=1)(=[O:17])=[O:18])[CH:7]=[C:6]2[CH2:5][CH2:4][C:3]([OH:35])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21226206Ethyl acetate hexaneHCID 58056548HCID 58056548, compound

Product 1

HCID 58056569HCID 58056569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 3-{5-chloro-1-[5-(4-trifluoromethyl-phenyl)-pyridine-3-sulfonyl]-1H-indol-3-yl}-propionic acid methyl ester 13 (20 mg, 0.00038 mol) was dissolved in 4 mL mixture of tetrahydrofuran:1N LiOH (4:1) and stirred vigorously overnight. TLC (20% ethyl acetate hexane) indicated absence of starting material and a new spot. The reaction was acidified by adding 1N HCl (pH 0-1 by pH paper) and extracted with 12 mL of ethyl acetate, which was dried over MgSO4. A silica plate was carried out using 2% methanol/chloroform to isolate the desired compound. 1H NMR consistent with structure. MS(ESI) [M−H+]−=507.02 (calculated 508.90).

Workup

  1. extractionextracted with 12 mL of ethyl acetate, which
  2. dry with materialwas dried over MgSO4

Sources & evidence

ORD record
ord-df07eae6af574e248548ebc2675a4729
Source dataset
uspto-grants-2011_11
Patent number
US08053463B2

Reaction notes

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