Lithium Hydroxide → HCID 70116272, compound

HRID 467678Notes

Reaction equation

HRID 467678 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][S:9][C:10]=1[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:5])C.[OH-].[Li+]>C1COCC1.C(O)C>[C:15]([O:14][C:12]([NH:11][C:10]1[S:9][N:8]=[N:7][C:6]=1[C:4]([OH:5])=[O:3])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70114251HCID 70114251, compound

Product 1

HCID 70116272HCID 70116272, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 5-tert-butoxycarbonylamino-[1,2,3]thiadiazole-4-carboxylic acid ethyl ester (0.87 g, 2.9 mmol) in a THF/ethanol mixture (18 ml; 3:1) was cooled to 0° C. and treated with lithium hydroxide (8.6 ml; 1N aqueous solution). After 15 min, the cooling bath was removed and the reaction mixture was stirred for 4 h at ambient temperature. The solvent was evaporated, and the residue was partitioned between diethylether (30 ml) and water (5 ml) and extracted. The aqueous phase was extracted with diethylether and the ether phases were washed with water. The combined aqueous phases were acidified with HCl (9 ml, 1N aqueous solution) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with water, dried and the solvent was evaporated to yield the product as colorless solid (0.66 g, 94%) which was used without any further purification.

Workup

  1. customthe cooling bath was removed
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between diethylether (30 ml) and water (5 ml)
  4. extractionextracted
  5. extractionThe aqueous phase was extracted with diethylether
  6. washthe ether phases were washed with water
  7. extractionextracted with dichloromethane (2×40 ml)
  8. washThe combined organic layers were washed with water
  9. customdried
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-915b0f0cd05e4b7ba9c6f5d3342f3f44
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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