Lithium Hydroxide → HCID 58465104, compound

HRID 2368288Notes

Reaction equation

HRID 2368288 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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][C:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[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 58465023HCID 58465023, compound

Product 1

HCID 58465104HCID 58465104, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-tert-butoxycarbonylamino-2-phenyl-thiazole-4-carboxylic acid ethyl ester (151 mg, 0.43 mmol) in a THF/ethanol mixture (3 ml; 2:1) was cooled to 0° C. and treated with lithium hydroxide (1.3 ml; 1N aqueous solution). After 15 min, the cooling bath was removed and the reaction mixture was stirred at 50° C. overnight. The reaction mixture was acidified with HCl (1.3 ml, 1N aqueous solution) and extracted with dichloromethane (2×10 ml). The combined organic layers were dried and the solvent was evaporated to yield the product as off-white solid (143 mg, 100%) which was used without any further purification.

Workup

  1. customthe cooling bath was removed
  2. extractionextracted with dichloromethane (2×10 ml)
  3. customThe combined organic layers were dried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d354e5ca8c404729b25675d0176863a7
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

Loading…