Triethylamine → 3-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide

HRID 749439ノート

反応式

HRID 749439 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:19][CH:20]=O)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].Cl.[NH:31]1[CH2:34][CH:33]([OH:35])[CH2:32]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:19][CH2:20][N:31]2[CH2:34][CH:33]([OH:35])[CH2:32]2)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 187156453-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl)-N-methyl-1-naphthamide

生成物 1

HCID 689772843-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide収率 80.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-1-naphthamide (see WO 00/02859; 1.0 g, 2.3 mmol) was dissolved in CH2Cl2 (10 mL) and to the resultant solution were added azetidin-3-ol hydrochloride (0.24 g, 2.2 mmol) and triethylamine (0.30 mL, 2.2 mmol). After stirring for 40 min, sodium triacetoxyborohydride (0.65 g, 3.1 mmol) was added and the solution was stirred at room temperature for 3 h. The solvent was removed by evaporation and the residue was partitioned between saturated aqueous NaHCO3 solution and ethyl acetate. The solvent was removed by evaporation and the residue was dissolved in hydrochloric acid (1M). The solution was washed with CH2Cl2, alkalised with aqueous NaOH (2M) and then extracted with CH2Cl2. The solvent was removed by evaporation and there was obtained 0.85 g (80%) of 3-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide as a white solid. 1H NMR (400 MHz, DMSO-d6): 0.8-4.4 (cm, 16H), 6.4-8.2 (cm, 8H), 8.6 (d, 1H); LCMS: m/z 482 (M+1)+.

後処理

  1. stirringthe solution was stirred at room temperature for 3 h
  2. customThe solvent was removed by evaporation
  3. customthe residue was partitioned between saturated aqueous NaHCO3 solution and ethyl acetate
  4. customThe solvent was removed by evaporation
  5. dissolutionthe residue was dissolved in hydrochloric acid (1M)
  6. washThe solution was washed with CH2Cl2
  7. extractionextracted with CH2Cl2
  8. customThe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-9927ad7f3a7541ba8ed7cc0779e43518
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

読み込み中…