2-Dimethylaminopyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

HRID 1089129ノート

反応式

HRID 1089129 の反応式
[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3].ClC(N(C)C)=C(C)C.[CH2:27]([O:30][C:31](=[O:67])[C:32]([N:52]1[C@H:55]([SH:56])[C@@H:54]([C@H:57]([O:59][C:60]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])[CH3:58])[C:53]1=[O:66])=[P:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:28]=[CH2:29].CN(C1C=CC=CN=1)C>C(Cl)Cl.[Ag].N1C=CC=CC=1>[CH2:27]([O:30][C:31](=[O:67])[C:32]([N:52]1[C@H:55]([S:56][C:14](=[O:16])[CH2:13][O:12][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[CH:18][CH:17]=2)[C@@H:54]([C@H:57]([O:59][C:60]([O:62][CH2:63][CH:64]=[CH2:65])=[O:61])[CH3:58])[C:53]1=[O:66])=[P:33]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:28]=[CH2:29]

参加物

8

反応物 4

HCID 218852-DimethylaminopyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 140845622-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl esterHCID 221604452-(4-{[(Prop-2-en-1-yloxy)carbonyl]amino}phenoxy)acetic acid

生成物 1

HCID 570957752-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester

試薬・触媒・溶媒 3

HCID 23954Silver触媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1 g of 4-(allyloxycarbonylamino)-phenoxyacetic acid is suspended in 2 ml of CH2Cl2 and 0.6 ml of 1-chloro-1-dimethylamino-2-methylprop-1-ene is added thereto. The mixture is stirred for 75 minutes and is then added dropwise, over a period of 5 minutes, to a solution of 1.74 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester, 50 mg of dimethylaminopyridine and 0.41 ml of pyridine in 30 ml of absolute methylene chloride. The title compound is obtained after working up analogously to Example 1.

出典と根拠

ORDレコード
ord-1d8f7f00493542e1ba237657de13eb2b
出典データセット
uspto-grants-1990_10
特許番号
US04965260

反応ノート

読み込み中…