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Dicyclohexylcarbodiimide → 2-[[[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[3-[(3,4-dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester

HRID 2292326
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HRID 2292326 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=O)[N:6]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O.[NH2:64][C@H:65]1[CH2:68][N:67]([C:69]([NH:71][S:72]([N:75]2[CH2:79][CH2:78][N:77]([NH:80][C:81](=[O:90])[C:82]3[CH:87]=[CH:86][C:85]([OH:88])=[C:84]([OH:89])[CH:83]=3)[C:76]2=[O:91])(=[O:74])=[O:73])=[O:70])[C:66]1=[O:92]>CN(C)C=O.C(N(CC)CC)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][C:13]([CH3:14])([CH3:15])[C:16]([O:18][CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])[C:8]([NH:64][CH:65]2[CH2:68][N:67]([C:69]([NH:71][S:72]([N:75]3[CH2:79][CH2:78][N:77]([NH:80][C:81](=[O:90])[C:82]4[CH:87]=[CH:86][C:85]([OH:88])=[C:84]([OH:89])[CH:83]=4)[C:76]3=[O:91])(=[O:73])=[O:74])=[O:70])[C:66]2=[O:92])=[O:10])[N:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 135359672-Amino-alpha-((2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy)imino)thiazol-4-acetic acidHCID 131715830(S)-3-amino-N-[[3-[(3,4-dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinyl]sulfonyl]-2-oxo-1-azetidinecarboxamide, trifluoroacetate salt

생성물 1

HCID 86742700
2-[[[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[3-[(3,4-dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, diphenylmethyl ester
수율 105.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

(Z)-2-Amino-α-[[1-(diphenylmethoxycarbonyl)-1-methylethoxy]imino]-4-thiazoleacetic acid (0.88 g, 0.002 mol) was dissolved in 20 ml of dimethylformamide followed by 0.3 g of N-hydroxybenzotriazole (containing 13% water), followed by 0.5 g of dicyclohexylcarbodiimide and 0.28 ml of triethylamine. The mixture was stirred at room temperature for 1 hour, then 1.08 g (0.002 mol) of (S)-3-amino-N-[[3-[(3,4-dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinyl]sulfonyl]-2-oxo-1-azetidinecarboxamide, trifluoroacetate salt (see Example 1D) was added. The mixture was stirred at room temperature overnight. The precipitate (dicyclohexylurea) was filtered off and the filtrate evaporated in vacuo. Trituration of the remaining syrup with ether yielded 1.8 g of the title compound in crude form.

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe precipitate (dicyclohexylurea) was filtered off
  3. customthe filtrate evaporated in vacuo

출처 및 근거

ORD 기록
ord-af9acfd90df5480288997b151415446e
출처 데이터셋
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04801705

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