Diethyl Pyrocarbonate → N-(3-hydroxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide

HRID 743151

反応式

HRID 743151 の反応式
C(NC(=O)[CH2:10][CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)C1C=CC=CC=1.C(N(CC)CC)C.Cl.[NH2:31][CH2:32][C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:35]([OH:43])[CH:34]=1.CC[O:46]C(OC(OCC)=O)=O>CN(C=O)C>[OH:43][C:35]1[CH:34]=[C:33]([CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38])[CH2:32][NH:31][C:10](=[O:46])[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1

参加物

6

反応物 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 3499346N-benzyl-4-(1H-indol-3-yl)butanamideHCID 22556073Methyl 4-aminomethylsalicylate hydrochloride

生成物 1

HCID 10360655N-(3-hydroxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A solution of 3-(3-indolyl)propanoic acid [II: R1 =R3 =H, R2 =(CH2)2COOH] (1.50 g), triethylamine (10 mL) and crude methyl 4-(aminomethyl)-2-hydroxybenzoate hydrochloride (3.46 g) in DMF (20 mL) was stirred at 20° C. for 10 minutes, then cooled to 0° C. DEPC (98%, 1.47 mL) was added, then the mixture was stirred at 20° C. for 17 hours. Workup and chromatography on silica gel, eluting with EtOAc:light petroleum (1:1) gave N-(3-hydroxy-4-methoxycarbonylbenzyl)-3-(3-indolyl)propanamide [II: R1 =R3 =H, R2 =(CH2)2CONHCH2Ph{3-OH, 4-COOMe}] (1.40 g, 50%); mp (EtOAc/light petroleum) 132°-133° C.

後処理

  1. washWorkup and chromatography on silica gel, eluting with EtOAc:light petroleum (1:1)

出典と根拠

ORDレコード
ord-ae0a8207e4784428bd545dfa33163243
出典データセット
uspto-grants-1996_09
特許番号
US05556874

関連ノート

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