m-Chloroperbenzoic acid → HCID 86605394、化合物

HRID 1180427ノート

反応式

HRID 1180427 の反応式
[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@H:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].ClC1C=C(C=CC=1)C(OO)=[O:37]>ClCCl>[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@@H:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N+:21]([O-:37])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 86605392HCID 86605392、化合物

生成物 1

HCID 86605394HCID 86605394、化合物収率 101.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-phenyl(4-pyridin-3-ylphenyl)methyl]oxy}pentanamide from example 38 (95 mg, 0.23 mmol) in dichloromethane (10 mL) was added 77% quality 3-chloroperoxybenzoic acid (51.5 mg, 0.23 mmol) at 5° C. The temperature was permitted to gradually rise to r.t. over 1.5 h. The mixture was concentrated and the residue partitioned between ethyl acetate and 1M Na2CO3. The ethyl acetate layer was dried (Na2SO4) and concentrated to yield 100 mg of the title compound. Purification by chromatography on silica gel using 10% methanol in dichloromethane and concentrating with diethyl ether 2 times gave a white solid.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and 1M Na2CO3
  3. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c5aebbd7014442929a2d9baa1d4c3fe5
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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