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

HRID 1170646ノート

反応式

HRID 1170646 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:39]=[CH:38][C:25]([C:26]([O:28]CC2C=CC(OC)=CC=2)=[O:27])=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.ICC1C=C(OCCOC(=O)[C@H](C(C)C)NC(OCC2C=CC=CC=2)=O)C=CC=1C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:39]=[CH:38][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 23387399iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acidHCID 233875454-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

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-c1d81a7d25bb418eb2a0073b8754843b
出典データセット
uspto-grants-2010_11
特許番号
US07825238B2

反応ノート

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