Acetic Acid → (E)-(6R,7R)-3-[1-(4-Amino-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-7-(2-phenylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597702노트

반응식

HRID 1597702 반응식
N1C=CN=C1.C(OC([NH:12][C:13]1[CH:49]=[CH:48][C:16]([CH2:17][N:18]2[CH2:22][CH2:21]/[C:20](=[CH:23]\[C:24]3[CH2:31][S:30][C@H:29]4[N:26]([C:27](=[O:43])[C@H:28]4[NH:32][C:33](=[O:42])[CH2:34][S:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:25]=3[C:44]([OH:46])=[O:45])/[C:19]2=[O:47])=[CH:15][CH:14]=1)=O)C=C.C[Si](/N=C(/O[Si](C)(C)C)\C(F)(F)F)(C)C.C(O)(=O)C.C([SnH](CCCC)CCCC)CCC.Cl>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[NH2:12][C:13]1[CH:49]=[CH:48][C:16]([CH2:17][N:18]2[CH2:22][CH2:21]/[C:20](=[CH:23]\[C:24]3[CH2:31][S:30][C@H:29]4[N:26]([C:27](=[O:43])[C@H:28]4[NH:32][C:33](=[O:42])[CH2:34][S:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:25]=3[C:44]([OH:46])=[O:45])/[C:19]2=[O:47])=[CH:15][CH:14]=1

참가 물질

9

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 5366669trimethylsilyl (1E)-2,2,2-trifluoro-N-trimethylsilylethanimidateHCID 69468988(E)-(6R,7R)-3-[1-(4-allyloxycarbonylamino-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-7-(2-phenylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid imidazole salt

생성물 1

HCID 69466517(E)-(6R,7R)-3-[1-(4-Amino-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-7-(2-phenylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

(E)-(6R,7R)-3- [1-(4-allyloxycarbonylamino-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-7-(2-phenylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid imidazole salt (1:1) (400.0 mg, 0.57 mmol) was suspended in 20 ml dichloromethane and treated with N,O-bis(trimethylsilyl)-trifluoroacetamide (240.7 ml, 9.11 mmol). After 15 min, bis(triphenylphosphine)palladium(II) chloride (10.0 mg, 0.014 mmol), acetic acid (0.65 ml, 11.4 mmol) and tributyltin hydride (1.53 ml, 5.70 mmol) were added. After 45 min the suspension was poured under stirring on 250 ml diethyl ether, containing 3 ml of a hydrochloric acid-saturated diethyl ether solution and was stirred for 1 h. The solid material was collected by filtration, suspended in 4 ml water: acetonitrile (1:1) and the pH was adjusted to 2 with 1M hydrochloric acid. To the suspension an equal amount of MCI gel (75-150μ, Mitsubishi Kasei Corporation) was added, the organic solvent was evaporated and the residue was chromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (9:1, 4:1, 2:1, 1:1, 1:3). The organic solvent was evaporated and the aqueous phase was freeze-dried.

후처리

  1. additionAfter 45 min the suspension was poured
  2. filtrationThe solid material was collected by filtration
  3. additionTo the suspension an equal amount of MCI gel (75-150μ, Mitsubishi Kasei Corporation) was added
  4. customthe organic solvent was evaporated
  5. customthe residue was chromatographed on MCI gel (75-150μ, Mitsubishi Kasei Corporation) with a gradient of water:acetonitrile (9:1, 4:1, 2:1, 1:1, 1:3)
  6. customThe organic solvent was evaporated
  7. customthe aqueous phase was freeze-dried

출처 및 근거

ORD 기록
ord-f19a5a1399bc474a8e94e2f1be75a3bb
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294668B1

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