Triethylamine → N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide

HRID 2395043

反応式

HRID 2395043 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.Cl.[CH3:43][NH:44][OH:45].CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[CH3:43][N:44]([OH:45])[C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:19][CH:20]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 77906N-methylhydroxylamine hydrochlorideHCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

生成物 1

HCID 18973882N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide収率 36.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-(3-(2-benzyloxyphenyl)propyl]benzoic acid (1.0 g), 1-HOBT (0.39 g) and DCCI (0.595 g) in DMF (10 ml) was stirred for 3 hours, then added to a solution of N-methylhydroxylamine HCl (0.24 g) and Et3N (0.29 g) in CH2Cl2 (10 ml) and stirred for 70 hours. The product was extracted in 2N aqueous KOH and washed with ethyl acetate. The aqueous solution was acidified with concentrated HCl and extracted with diethyl ether. The solvent was evaporated and the residue subjected to flash chromatography on silica gel (using diethyl ether:methanol (95:5) as eluant) to give N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide as a gum (0.39 g).

後処理

  1. stirringstirred for 70 hours
  2. extractionThe product was extracted in 2N aqueous KOH
  3. washwashed with ethyl acetate
  4. extractionextracted with diethyl ether
  5. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-5bfdfe74464e4b01b0b7df5c5b5d7ece
出典データセット
uspto-grants-1998_09
特許番号
US05811459

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