Water → Ethyl 2-[[(1,1-dimethylpropoxy)carbonyl]amino]-4-thiazoleacetate

HRID 325363Notes

Reaction equation

HRID 325363 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(OCC)C.Cl[C:19]([O:21][C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])=[O:20].O>N1C=CC=CC=1.C(Cl)Cl>[C:22]([O:21][C:19]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)=[O:20])([CH2:25][CH3:26])([CH3:24])[CH3:23]

Participants

8

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 150513282-Methylbutan-2-yl carbonochloridate2×HCID 178470764HCID 178470764, compound

Product 1

HCID 19978738Ethyl 2-[[(1,1-dimethylpropoxy)carbonyl]amino]-4-thiazoleacetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (14 g.) in a mixture of pyridine (40 g.) and methylene chloride (300 ml.) was gradually added diethyl ether solution of tert-pentyl chloroformate (70 ml.) containing 0.35 mole of tert-pentyl chloroformate over 10 minutes at -20° C. with stirring, and the mixture was stirred for 2 hours at the same temperature and further stirred for 0.5 hour at 0° C. After the reaction, the reaction mixture was poured into water (200 ml.), and then the organic layer was separated. The organic layer was washed with 2 N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water in turn and then dried over magnesium sulfate. The solvent was distilled off from the organic layer to give dark brown oil of ethyl 2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (12 g.).

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. stirringfurther stirred for 0.5 hour at 0° C
  3. customAfter the reaction
  4. customthe organic layer was separated
  5. washThe organic layer was washed with 2 N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water in turn
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off from the organic layer

Sources & evidence

ORD record
ord-5c97246ed8f147dea1ac3fc95a6bb469
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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