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Trifluoroacetic acid → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyiminoacetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1032189
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HRID 1032189 반응식
C1(C([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)[C@H:20]([NH:38][C:39](=[O:87])/[C:40](/[C:62]2[N:63]=[C:64]([NH:67]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:65][CH:66]=2)=[N:41]\[O:42][C:43](=[O:61])[C:44]2[CH:49]=[C:48]([O:50][C:51](=[O:54])[CH2:52][Cl:53])[C:47]([O:55][C:56](=[O:59])[CH2:57][Cl:58])=[CH:46][C:45]=2[CH3:60])[C:19]3=[O:88])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClC(Cl)C>[NH2:67][C:64]1[S:65][CH:66]=[C:62](/[C:40](=[N:41]/[O:42][C:43](=[O:61])[C:44]2[CH:49]=[C:48]([O:50][C:51](=[O:54])[CH2:52][Cl:53])[C:47]([O:55][C:56](=[O:59])[CH2:57][Cl:58])=[CH:46][C:45]=2[CH3:60])/[C:39]([NH:38][C@@H:20]2[C:19](=[O:88])[N:18]3[C@@H:21]2[S:22][CH2:23][C:24]([CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:87])[N:63]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 16166549benzhydryl (6R,7R)-7-[[(2Z)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

생성물 1

HCID 14124722
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyiminoacetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
수율 93.3%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of the product obtained in Step 5 (0.47 g) in dichloroethane (3.5 ml) were added anisole (0.23 ml) and trifluoroacetic acid (0.47 ml) under ice cooling, and the resulting solution was stirred at room temperature for five hours. After removing the solvent under reduced pressure, the residue was crystallized with ether, giving 0.3 g of the objective compound (as trifluoroacetic acid salt).

후처리

  1. customAfter removing the solvent under reduced pressure
  2. customthe residue was crystallized with ether

출처 및 근거

ORD 기록
ord-536a286ee74e48deb5260c0a73209abe
출처 데이터셋
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04956474

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