Sodium Hydroxide → HCID 67194792, compound

HRID 1891474Notes

Reaction equation

HRID 1891474 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][CH2:28][C:29]([O:31]C)=[O:30])=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C>[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][CH2:28][C:29]([OH:31])=[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 67195352HCID 67195352, compound

Product 1

HCID 67194792HCID 67194792, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (R)-methyl 2-((4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetate (100 mg, 0.22 mmol) in ethanol was added 2N NaOH (1.1 mL) and the mixture stirred at room temperature for 12 h. The solvent was evaporated and the residue dissolved in water and acidified with 1N HCl. The resulting solid was filtered and dried to give 60 mg (63%) of (R)-2-((4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetic acid 96 as yellow-green solid. LCMS-ESI (m/z) calculated for C24H23N3O3S: 433.1; found 434.2 [M+H]+, tR=2.61 min.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-d5846b458efb471786a3bfc168c6655e
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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