tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine benzyl ester → tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine

HRID 1759191ノート

反応式

HRID 1759191 の反応式
C([O:8][C:9](=[O:42])[CH2:10][NH:11][C:12](=[O:41])[C@@H:13]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:14][C:15](=[O:33])[C@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C1C=CC=CC=1>CO.[Pd]>[C:21]([O:20][C:18]([NH:17][C@H:16]([C:15]([NH:14][C@@H:13]([C:12]([NH:11][CH2:10][C:9]([OH:42])=[O:8])=[O:41])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

参加物

4

反応物 1

HCID 57281973tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine benzyl ester

生成物 1

HCID 57232727tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine収率 89.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

23.0 g (40 mmoles) of the protected tripeptide ester obtained in Step 2 above are dissolved in 40 ml of methanol, and the mixture is hydrogenated in the presence of palladium-on-carbon catalyst. At the end of the reaction the catalyst is filtered off, washed with methanol, the filtrate and the wash are combined and evaporated under reduced pressure. The residue is triturated with diethyl ether, the solid is filtered off, washed with diethyl ether and dried in a vacuum desiccator. 17.45 g (89.8%) of tert.-butoxycarbonyl-L-tyrosyl-D-phenylalanyl-glycine are obtained; m.p.: 105°-110° C., Rf13 =0.2-0.3.

後処理

  1. customAt the end of the reaction the catalyst
  2. filtrationis filtered off
  3. washwashed with methanol
  4. customevaporated under reduced pressure
  5. customThe residue is triturated with diethyl ether
  6. filtrationthe solid is filtered off
  7. washwashed with diethyl ether
  8. customdried in a vacuum desiccator

出典と根拠

ORDレコード
ord-833d405a33224c708f23ff5161ee782c
出典データセット
uspto-grants-1982_07
特許番号
US04339440

反応ノート

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