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 1597702ノート

反応式

HRID 1597702 の反応式
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

参加物

9

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-f19a5a1399bc474a8e94e2f1be75a3bb
出典データセット
uspto-grants-2001_09
特許番号
US06294668B1

反応ノート

読み込み中…