Water → 5-(1-(2-(benzyloxycarbonyl-N-methylamino)-3-methylbutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione

HRID 1988264ノート

反応式

HRID 1988264 の反応式
C(OC([NH:11][CH:12]([CH:25]1[NH:29][C:28](=[O:30])[NH:27][C:26]1=[O:31])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=1)=O)C1C=CC=CC=1.[H][H].[C:34]([N:44]([CH3:52])[C@H:45]([C:49]([OH:51])=O)[CH:46]([CH3:48])[CH3:47])([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].O>CO.C1COCC1.[C].[Pd]>[CH2:37]([O:36][C:34]([N:44]([CH:45]([CH:46]([CH3:47])[CH3:48])[C:49]([NH:11][CH:12]([CH:25]1[NH:29][C:28](=[O:30])[NH:27][C:26]1=[O:31])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([CH3:24])([CH3:22])[CH3:23])[CH:15]=1)=[O:51])[CH3:52])=[O:35])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

8

反応物 4

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 178191965-(1-(Benzyloxycarbonylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dioneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 178192035-(1-(2-(benzyloxycarbonyl-N-methylamino)-3-methylbutyrylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione収率 53%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(1-(benzyloxycarbonylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione (543 mg, 1.28 mmol) in methanol (10 ml), 10% palladium carbon (55 mg) was added and stirred at room temperature in a hydrogen atmosphere for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; to a solution of the thus obtained residue in THF (13 ml), Z-N-Me-Val-OH (509 mg, 1.92 mmol), CMPI (491 mg, 1.92 mmol) and TEA (0.535 ml, 3.84 mmol) were added under cooling with ice and stirred at room temperature for 3 hours. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=2:1), giving the titled compound (365 mg, 53%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. temperatureunder cooling with ice
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure

出典と根拠

ORDレコード
ord-c025ded60aff44f180aa99246975f9c1
出典データセット
uspto-grants-2009_06
特許番号
US07553969B1

反応ノート

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