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

HRID 1790808노트

반응식

HRID 1790808 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-61a76cca51a74f099b8435aaf4b84a1d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071173B2

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