Lithium hydroxide, monohydrate → 605667-95-6

HRID 901948Notes

Reaction equation

HRID 901948 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[N:10]=[C:11]([CH:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[S:12][CH:13]=1)=[O:8])C>C1COCC1.O>[C:19]([O:18][C:17](=[O:23])[NH:16][CH:14]([C:11]1[S:12][CH:13]=[C:9]([C:7]([OH:8])=[O:6])[N:10]=1)[CH3:15])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 485035HCID 485035, compound

Product 1

HCID 21634039605667-95-6Yield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (165 mg, 3.9 mmol) was added to a solution of tert-butyl (1-(4-(ethyloxycarbonyl)thiazol-2-yl)ethyl)carbamate (1.4 g crude material) in THF (25 ml) and water (20 ml) and stirred at room temperature for 18 h. A further amount of lithium hydroxide monohydrate was added (165 mg) and stirring continued for 4 h. The THF was removed in vacuo, the aqueous residue acidified with 1N hydrochloric acid and extracted twice with chloroform. The combined organic layers were washed with brine, dried and reduced. Chromatography (50:2:1 chloroform, methanol, acetic acid) and recrystallisation (EtOAc/hexanes) afforded tert-butyl(1-(4-carboxythiazol-2-yl)ethyl)carbamate (686 mg, 64% over two steps).

Workup

  1. stirringstirring
  2. waitcontinued for 4 h
  3. customThe THF was removed in vacuo
  4. extractionextracted twice with chloroform
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. customChromatography (50:2:1 chloroform, methanol, acetic acid) and recrystallisation (EtOAc/hexanes)

Sources & evidence

ORD record
ord-6d8a7c14de334dc28882b2d0437a49b0
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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