Trifluoroacetic acid → 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

HRID 1790808ノート

反応式

HRID 1790808 の反応式
FC(F)(F)C(O)=O.IC[C:10]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][O:22][C:23](=[O:39])[C@H:24]([CH:36]([CH3:38])[CH3:37])[NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>ClCCl>[CH2:29]([O:28][C:26]([NH:25][C@H:24]([C:23]([O:22][CH2:21][CH2:20][O:19][C:17]1[CH:18]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=1)=[O:39])[CH:36]([CH3:38])[CH3:37])=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 23387399iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

生成物 1

HCID 233875344-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-methoxybenzyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy) benzoate (10.2 g, 19.04 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred 3 hours at room temperature. The solution was evaporated under reduced pressure and co-evaporated two times with toluene. The product was isolated by silica gel column chromatography. Yield: 6.9 g=87%. The product may be activated and esterified direct to a drug or converted to iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid as described above, that is by treatment with a base, chloroiodomethane, separation and then treatment with NaI.

後処理

  1. customThe solution was evaporated under reduced pressure
  2. customThe product was isolated by silica gel column chromatography
  3. customthat is by treatment with a base, chloroiodomethane, separation

出典と根拠

ORDレコード
ord-61a76cca51a74f099b8435aaf4b84a1d
出典データセット
uspto-grants-2006_07
特許番号
US07071173B2

反応ノート

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