Sodium Hydroxide → HCID 58367327, compound

HRID 1891472Notes

Reaction equation

HRID 1891472 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:27][C:26]([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:25][CH:24]=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:27][C:26]([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:25][CH:24]=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 58367210HCID 58367210, compound

Product 1

HCID 58367327HCID 58367327, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-methyl 2-((tert-butoxycarbonyl)(4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetate (120 mg, 0.22 mmol) in MeOH (2 mL) was added 6N 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 110 mg (94%) of (S)-2-((tert-butoxycarbonyl)(4-(2-(3-cyano-4-isopropoxyphenyl)thiazol-5-yl)-2,3-dihydro-1H-inden-1-yl)amino)acetic acid as white solid which was used in the next experiments without purification. LCMS-ESI (m/z) calculated for C29H31N3O5S: 533.2; found 534.2 [M+H]+, tR=3.92 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-efb7ff62c664482cb50c7b31907a2f52
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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