Water → HCID 68183233, compound

HRID 1615540Notes

Reaction equation

HRID 1615540 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:19]1[N:20]=[C:21]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[S:22][C:23]=1[C:24]([O:26]CC)=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:19]1[N:20]=[C:21]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[S:22][C:23]=1[C:24]([OH:26])=[O:25])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68183404HCID 68183404, compound

Product 1

HCID 68183233HCID 68183233, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{3-[(tert-butoxycarbonyl)amino]-1-(4-chlorophenyl)propyl}-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylate (0.322 g, 0.631 mmol) in THF (7.8 mL) and MeOH (2.6 mL) was added a solution of sodium hydroxide in water (1 M, 7.76 mL, 7.76 mmol). The solution was stirred at room temperature for 3 days. The solvents were evaporated and the residue was diluted with water then 1N hydrogen chloride aqueous solution was added until pH 7 was reached. The mixture was extracted twice with EA and the combined organic layers were washed with brine then dried over anhydrous sodium sulfate and concentrated to give the product (0.321 g, 105%) which was used directly in the next step. LCMS: (AA) ES+ 482, 484.

Workup

  1. customThe solvents were evaporated
  2. additionthe residue was diluted with water
  3. addition1N hydrogen chloride aqueous solution was added until pH 7
  4. extractionThe mixture was extracted twice with EA
  5. washthe combined organic layers were washed with brine
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7556a005e3649849b82872e87eb7485
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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