Water → HCID 58459773, compound

HRID 1675347Notes

Reaction equation

HRID 1675347 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[CH2:15][C:14]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C:13]=3[CH2:12]2)=[N:8][CH:7]=1)=[O:5])C.O.[OH-].[Li+].O>C1COCC1>[C:4]([C:6]1[S:10][C:9]([N:11]2[CH2:15][C:14]3[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][C:13]=3[CH2:12]2)=[N:8][CH:7]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 58459770HCID 58459770, compound

Product 1

HCID 58459773HCID 58459773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 5-(5-ethoxycarbonylthiazol-2-yl)-3,4,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-2-carboxylate (1.34 g, 3.66 mmol) and lithium hydroxide hydrate (385 mg, 9.17 mmol) were stirred in 150 ml of THF and 50 ml of water at 50° C. for 2 h and at 80° C. for 8 h. THF was concentrated under reduced pressure and the water phase was extracted with ethyl acetate. The water phase was acidified and extracted again with ethyl acetate. The organic phase was concentrated. Yield: 662 mg (53%), M+H+: 338.10.

Workup

  1. concentrationTHF was concentrated under reduced pressure
  2. extractionthe water phase was extracted with ethyl acetate
  3. extractionextracted again with ethyl acetate
  4. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-7a0670c6ee844af6b8ae9ede10776b61
Source dataset
uspto-grants-2011_08
Patent number
US08003677B2

Reaction notes

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