Sodium Hydroxide → HCID 53232982, compound

HRID 1891483Notes

Reaction equation

HRID 1891483 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@@H:22]4[NH:27][S:28]([CH2:31][C:32]([O:34]C)=[O:33])(=[O:30])=[O:29])=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][C@@H:22]4[NH:27][S:28]([CH2:31][C:32]([OH:34])=[O:33])(=[O:29])=[O:30])=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58367119HCID 58367119, compound

Product 1

HCID 53232982HCID 53232982, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared using General Procedure 15: To a stirred solution containing (S)-methyl 2-(N-(4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)sulfamoyl)acetate (11.2 mg, 0.02 mmol) in MeOH (1 mL) was added 6N NaOH (100 uL). After 1 h, the crude reaction was concentrated and the product purified by preparative HPLC to give 5 mg (45%) of (S)-2-(N-(4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)sulfamoyl)acetic acid 159 as light yellow solid. LCMS-ESI (m/z) calculated for C24H23N3O5S2: 497.1; found 498.1 [M+H]+, tR=3.44 min.

Workup

  1. customPrepared
  2. customthe crude reaction
  3. concentrationwas concentrated
  4. customthe product purified by preparative HPLC

Sources & evidence

ORD record
ord-ca7f38943ec948e0b5819dd5a6586dec
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

Loading…