Trifluoroacetic acid → N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio)-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine

HRID 254112ノート

反応式

HRID 254112 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20](OC)=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:25]2[CH:35]=[CH:34][C:28]([O:29][CH2:30]C(O)=O)=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.Cl.NC[C:39]([NH:41][C@@H:42]([C:46]([O:48]C(C)(C)C)=[O:47])C(C)C)=[O:40].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)[F:78].FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([F:78])=[CH:21][CH:22]=3)=[O:16])[C@H:9]2[C:25]2[CH:26]=[CH:27][C:28]([O:29][CH2:30][C:39]([NH:41][CH2:42][C:46]([OH:48])=[O:47])=[O:40])=[CH:34][CH:35]=2)=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66842884[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-methoxyphenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acidHCID 86613090tert-butyl glycyl-D-valinate hydrochloride

生成物 1

HCID 66842760N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio)-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine収率 89.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of [4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-methoxyphenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acid (0.0153 g, 0.031 mmol), tert-butyl glycyl-D-valinate hydrochloride (0.0099 g, 0.037 mmol) and N-methylmorpholine (0.010 ml, 0.091 mmol) in DCM (2 ml) was stirred at room temperature. TBTU (0.016 g, 0.050 mmol) was added and the mixture was stirred for 3.5 h. Trifluoroacetic acid (0.5 ml) was added and after 3.5 h the solvent was removed under reduced pressure. The residue was purified by preparative HPLC on a Kromasil C8-column using a gradient of 5-100% MeCN in 0.15% trifluoroacetic acid buffer as eluent. The solvent was removed under reduced pressure and 0.015 g (74%) of the title product was obtained. M/z 652.20.

後処理

  1. stirringthe mixture was stirred for 3.5 h
  2. customwas removed under reduced pressure
  3. customThe residue was purified by preparative HPLC on a Kromasil C8-column
  4. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-03adb862790142d9a2dca76e28d169ab
出典データセット
uspto-grants-2011_01
特許番号
US07871998B2

反応ノート

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