Hydrochloric Acid → Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me

HRID 1988240ノート

反応式

HRID 1988240 の反応式
[NH:1]([CH3:22])[C@H:2]([C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C:23]([N:33]([CH3:41])[C@H:34]([C:38]([OH:40])=O)[CH:35]([CH3:37])[CH3:36])([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].O.Cl>C1COCC1>[C:23]([N:33]([CH3:41])[C@H:34]([C:38]([N:1]([CH3:22])[C@H:2]([C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=1)=[O:40])[CH:35]([CH3:36])[CH3:37])([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131727507N-Me-Tyr(3-t-Bu)-NHSO2Me

生成物 1

HCID 131727506Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the crude N-Me-Tyr(3-t-Bu)-NHSO2Me (0.51 g, 1.43 mmol), Z-N-Me-Val-OH 0.49 g, 1.86 mmol) and CMPI (0.51 g, 2.00 mmol) in THF (10 ml), TEA (0.60 ml, 4.29 mmol) was added under cooling with ice and stirred at room temperature overnight. The reaction mixture was mixed with water, rendered acidic by the addition of 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over 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=2:3 containing 0.5% acetic acid) to give the titled compound (0.70 g, in 2 steps, 85%).

後処理

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

出典と根拠

ORDレコード
ord-27a2dd35c4b941e0af89ee128a266e4f
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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