Sodium Hydroxide → HCID 11155768, compound

HRID 602779Notes

Reaction equation

HRID 602779 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[C:8]([C:10]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)[F:11])[O:7][N:6]=1)=[O:4].[OH-].[Na+].[NH4+].[Cl-]>CO.C1COCC1.O>[C:28]1([S:25]([C:10]([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)([F:11])[C:8]2[O:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[N:9]=2)(=[O:27])=[O:26])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 11317811HCID 11317811, compound

Product 1

HCID 11155768HCID 11155768, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of 600 mg (1.22 mmol) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester in 5 mL of MeOH/THF 1:1, were added 980 mg (24.5 mmol, 20 eq) of NaOH in solution in 3 mL of water. After 2 hours at RT, aqueous NH4Cl was added until pH=7 was reached, the product was extracted with EtOAc, dried over Na2SO4, filtered and solvent evaporated. Column chromatography on silica gel with CH2Cl2/MeOH 8:2 yielded 300 mg (52%) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b ]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid as a white solid, MS: 430 (M-COOH).

Workup

  1. extractionthe product was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-3965ca6fe64347b9bcd2cd1dc79a505a
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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