Sodium Hydroxide → HCID 53232876, compound

HRID 1891482Notes

Reaction equation

HRID 1891482 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([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]CC)=[O:33])(=[O:30])=[O:29])=[N:15][N:14]=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:17][C:16]([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])=[N:15][N:14]=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 58367132HCID 58367132, compound

Product 1

HCID 53232876HCID 53232876, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared using General Procedure 15: To a stirred solution of (S)-ethyl 2-(N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)sulfamoyl)acetate (75 mg, 0.8 mmol) in MeOH (4 mL) was added 6N NaOH (0.12 mL). After 3 h, the crude reaction was concentrated then partitioned between DCM/IPA and 1N HCl. The organic layer was dried over MgSO4 and concentrated to give 43 mg (60%) of (S)-2-(N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)sulfamoyl)acetic acid 40 as light yellow solid. LCMS-ESI (m/z) calculated for C23H22N4O5S2: 498.1; found 499.1 [M+H]+, tR=3.34 min.

Workup

  1. customPrepared
  2. customthe crude reaction
  3. concentrationwas concentrated
  4. customthen partitioned between DCM/IPA and 1N HCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2cf5815f2b04f86b1f1d27cf8ed120d
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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