Sodium Hydroxide → HCID 58367245, compound

HRID 1891471Notes

Reaction equation

HRID 1891471 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:14]1[C:22]2[C:17](=[C:18]([C:23]3[S:24][C:25]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[C:30]([C:38]#[N:39])[CH:29]=4)=[N:26][N:27]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)[CH2:9][C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([C@@H:14]1[C:22]2[C:17](=[C:18]([C:23]3[S:24][C:25]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:36])[CH3:37])=[C:30]([C:38]#[N:39])[CH:29]=4)=[N:26][N:27]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58367159HCID 58367159, compound

Product 1

HCID 58367245HCID 58367245, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-methyl 2-((tert-butoxycarbonyl)(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetate (120 mg, 0.21 mmol) in MeOH (2 mL) was added 6N solution of sodium hydroxide (180 μL) and the mixture was stirred at room temperature for overnight. The solvent was evaporated and the residue was dissolved in water (5 mL) and acidified with 1N HCl. The mixture was extracted with EA (3×5 mL) and the organic layers washed with brine, dried over MgSO4, and concentrated to afford 108 mg (92%) of (S)-2-((tert-butoxycarbonyl)(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1yl)amino)acetic acid as white solid which was used in the next experiments without purification. LCMS-ESI (m/z) calculated for C28H30N4O5S: 534.2; found no M+, tR=3.81 min.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (5 mL)
  3. extractionThe mixture was extracted with EA (3×5 mL)
  4. washthe organic layers washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bad5e4dd3c1481c916256cdc3d7e707
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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