Water → (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide

HRID 2201050

反応式

HRID 2201050 の反応式
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([O:18][CH2:19][C@H:20]([C:22]([NH2:24])=[O:23])[NH2:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[CH2:11]([O:18][CH2:19][C@@H:20]([NH:21][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Br:1])[CH:9]=1)[C:22]([NH2:24])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 58987402O-benzyl-D-serinamide

生成物 1

HCID 67509048(R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide収率 17.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), O-benzyl-D-serinamide (290 mg, 1.49 mmol) and DIEA (0.466 mL, 2.68 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-60% EtOAc in hexane to give (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg).

後処理

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 0-60% EtOAc in hexane

出典と根拠

ORDレコード
ord-7b1a324529b0441bba81e652b653dea6
出典データセット
uspto-grants-2016_06
特許番号
US09359375B2

関連ノート

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