Hydrochloric Acid → [[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid, diphenylmethyl ester

온도

-30 °C

Into a -30° C. cold mixture of 0.66 g (1.5 mmol) of (Z)-2-amino-α-[[1-(diphenylmethoxycarbonyl)-1-methylethoxy]imino]-4-thiazoleacetic acid in 13 ml of dry dimethylformamide, 0.63 ml (4.5 mmol) of triethylamine was dropped, followed by 0.33 ml (1.5 mmol) of diphenylchlorophosphate. After stirring at -30° C. for 1 hour, 0.42 ml (3.0 mmol) of triethylamine was dropped in, followed by the addition of 0.80 g (1.5 mmol) of (S)-3-amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine. The mixture was stirred for 2 hours at -10° C. and an additional 2 hours at 0° C. The solvent was removed in vacuo and the residue was taken up in a few ml of ethyl acetate and ice water. The pH of the mixture was corrected to pH=2 the addition of dilute hydrochloric acid. The insoluble material was collected by suction1) and stirred with a few ml of ethyl acetate until it became crystalline; yield after drying in vacuo: 0.31 g. This material was used in the next step without further purification.

1. additionwas dropped
2. stirringThe mixture was stirred for 2 hours at -10° C. and an additional 2 hours at 0° C
3. customThe solvent was removed in vacuo
4. customThe insoluble material was collected by suction1) and
5. customyield
6. customafter drying in vacuo
7. customThis material was used in the next step without further purification

ORD 기록

ord-67bc1040828745be9fd73b0c6a547f28

출처 데이터셋

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04801705