Water → Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1383744ノート

反応式

HRID 1383744 の反応式
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26].O.C(OCC)(=O)C>C1COCC1.ClC(OCC(C)C)=O.CN1CCOCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:41])[CH3:42])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

8

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

生成物 1

HCID 131722753Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

試薬・触媒・溶媒 3

HCID 79724-Methylmorpholine溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 62365Isobutyl chloroformate溶媒

実験手順

To a solution of Z-Phe-OH (742 mg) in THF (3 ml), isobutyl chloroformate (0.32 ml) and NMM (0.27 ml) were added under cooling with ice and the mixture was stirred for 15 minutes. Subsequently, a solution of N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (600 mg) in THF (3 ml) was added and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture and extraction was effected with ethyl acetate. The extract was washed with saturated brine, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2) to give Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 611 mg (58%).

後処理

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 10 hours
  3. washThe extract was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2)

出典と根拠

ORDレコード
ord-e8669919cca647fb9505c605464bfc23
出典データセット
uspto-grants-2001_07
特許番号
US06255285B1

反応ノート

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