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

HRID 1383716ノート

反応式

HRID 1383716 の反応式
[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:20][C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([NH:20][C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:31])[CH3:32])[CH:24]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

7

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131722727Tyr(3-tBu)-NH2

生成物 1

HCID 131722729Z-N-Me-Val-Tyr(3-tBu)-NH2収率 131.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 400 mg (1.52 mmol) of Z-N-Me-Val-OH, 300 mg (1.27 mmol) of Tyr(3-tBu)-NH2 and 230 mg (1.52 mmol) of HOBT in 7 ml of DMF, 0.24 ml (1.52 mmol) of DIC was added dropwise under cooling with ice and the mixture was stirred at room temperature for 15 hours and a half. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of methylene chloride, methanol and aqueous ammonia at a ratio of 100:3:1) to give 810 mg of Z-N-Me-Val-Tyr(3-tBu)-NH2.

後処理

  1. temperatureunder cooling with ice
  2. washwashed with saturated brine
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluting solvent

出典と根拠

ORDレコード
ord-d2c90f2d62b942e4bda4e886686cd2c0
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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