Water → 1-Cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 2370916ノート

反応式

HRID 2370916 の反応式
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[N:15]=[CH:16][N:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:18]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH:25]1([O:31][C:32]([O:34][CH:35](Cl)[CH3:36])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH:10]([C:14]2[N:15]=[CH:16][N:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:18]=2)[C:11]([O:13][CH:35]([O:34][C:32]([O:31][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:33])[CH3:36])=[O:12])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 694540453-(6-Aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionic acid hydrochloride

生成物 1

HCID 116487441-Cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate収率 41.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 50.0 mg (0.16 mmol) of the compound from example 1i and 39 mg (0.19 mmol) of 1-cyclohexyloxycarbonyloxy-1-ethyl chloride, 13 mg (0.08 mmol) of KI and 26 mg (0.19 mmol) of K2CO3 in 2 ml of DMF was stirred at 60° C. for 12 h. Then 5 ml of water were added and the reaction solution was extracted several times with EA. The combined EA extracts were dried, filtered and concentrated to dryness. The resulting residue was purified on silica gel with CH2Cl2/methanol as mobile phase, resulting in 32 mg of the title compound in the form of an amorphous solid.

後処理

  1. extractionthe reaction solution was extracted several times with EA
  2. dry with materialThe combined EA extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified on silica gel with CH2Cl2/methanol as mobile phase

出典と根拠

ORDレコード
ord-cc0d635853b74da9a230ff0d40108b32
出典データセット
uspto-grants-2014_04
特許番号
US08710232B2

反応ノート

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