Sodium Hydroxide → HCID 67014565, compound

HRID 1433077Notes

Reaction equation

HRID 1433077 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:25][C:24]4[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:23]=4[CH:22]=3)(=[O:20])=[O:19])[CH2:14][C:13]2=[O:31])[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:23]2[CH:22]=[C:21]([S:18]([N:15]3[CH2:16][CH2:17][N:12]([CH2:11][C:8]4[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=4)[C:13](=[O:31])[CH2:14]3)(=[O:20])=[O:19])[S:25][C:24]=2[CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67014127HCID 67014127, compound

Product 1

HCID 67014565HCID 67014565, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl-carboxylic acid ethyl ester (75 mg, 0.15 mmol) is dissolved in THF/MeOH −3:1 (2 mL) and a solution of 1N NaOH is added (0.5 mL). The reaction is stirred for 2 h and then diluted with EtOAc and washed with 2N HCl. The organic phase is dried (MgSO4) and concentrated to yield 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ 8.32 (d, 1H), 8.26 (s, 1H), 8.18 (s, 1H), 8.04 (d, 1H), 7.57 (dd, 1H), 4.74 (s, 2H), 3.87 (s, 2H), 3.49 (s, 4H); MS (Ion Spray) 471 (M)+.

Workup

  1. washwashed with 2N HCl
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c88a4b1b087844d3a6cad60bfa31eb4c
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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