2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

Base Information

Chemical Name:2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester
CAS No.:158743-65-8
Molecular Formula:C₂₅H₂₅ClN₂O₅S
Molecular Weight:501.003
Hs Code.:

Synonyms:2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

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Chemical Property of 2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

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Technology Process of 2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

There total 1 articles about 2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 79-04-9
chloroacetyl chloride

: diphenylmethyl 2-(2-tert-butoxycarbonylaminothiazol-4-yl)acetate

: 158743-65-8
2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

Guidance literature:: With lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min, 2.) THF, 1 h;
DOI:10.7164/antibiotics.47.453

Reference yield: 65.0%

: 75849-83-1
sodium 1,2,3-thiadiazole-5-thiolate

: 158743-65-8
2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

: 158743-63-6
2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-3-oxo-4-([1,2,3]thiadiazol-5-ylsulfanyl)-butyric acid benzhydryl ester

Guidance literature:: In ethanol; at 0 ℃; for 2h;
DOI:10.7164/antibiotics.47.453

Reference yield:

: 158743-65-8
2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

: diphenylmethyl 7β-<(E)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / ethanol / 2 h / 0 °C

2: NaBH₄ / methanol; CH₂Cl₂ / 0.33 h / -20 °C

3: 1.) TEA, methanesulfonyl chloride, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, ice-water cooling, 30 min, 2.) CH₂Cl₂, ice-water cooling, 20 min

4: 78 percent / trifluoroacetic acid / CH₂Cl₂; various solvent(s) / 2 h / 0 - 5 °C

5: 34.3 percent / N-methylmorpholine, phenylphosphoryl dichloride / CH₂Cl₂ / 2 h / -30 - -20 °C

With 4-methyl-morpholine; P,P-dichlorophenylphosphine oxide; sodium tetrahydroborate; TEA; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; ethanol; dichloromethane;
DOI:10.7164/antibiotics.47.453