Water → (S)-3-(1-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethyl)-8-chloroisoquinoline-1-carboxylic acid

HRID 1626936ノート

反応式

HRID 1626936 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=[O:13])=[N:9][C:8]([C@@H:14]([NH:16][C:17](=[O:33])[O:18][CH2:19][CH:20]1[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:15])=[CH:7]2.[OH:34]OS([O-])=O.[K+].O>CN(C=O)C>[CH:22]1[C:21]2[CH:20]([CH2:19][O:18][C:17]([NH:16][C@H:14]([C:8]3[N:9]=[C:10]([C:12]([OH:34])=[O:13])[C:11]4[C:6]([CH:7]=3)=[CH:5][CH:4]=[CH:3][C:2]=4[Cl:1])[CH3:15])=[O:33])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 86677063(S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate

生成物 1

HCID 71232891(S)-3-(1-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethyl)-8-chloroisoquinoline-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate (348) (12.0 g, 26.3 mmol, 1.0 eq) in DMF (150 mL), OXONE (30 g, 48.78 mmol, 1.85 eq) was added and the resulting mixture was stirred at RT over night. The mixture was poured into water (600 mL) and then filtered. The solid was dissolved in ethyl acetate (100 mL), and then PE (300 mL) was added dropwise to this solution. The precipitate was collected by filtration to afford (S)-3-(1-(((9H-fluoren-9-yl)methoxy)carbonylamino)ethyl)-8-chloroisoquinoline-1-carboxylic acid (349).

後処理

  1. filtrationfiltered
  2. dissolutionThe solid was dissolved in ethyl acetate (100 mL)
  3. additionPE (300 mL) was added dropwise to this solution
  4. filtrationThe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-8490771fb7f34a06b2a73c16fb16dc5b
出典データセット
uspto-grants-2014_07
特許番号
US08785470B2

反応ノート

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