Benzoic Acid → HCID 54529925、化合物

HRID 1379553ノート

反応式

HRID 1379553 の反応式
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24].[C:25](O)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN(C)CCCN=C=NCC>ClCCl>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:23])([C:7]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:25](=[O:32])[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:17]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:24]

参加物

5

反応物 3

HCID 243Benzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54238570HCID 54238570、化合物

生成物 1

HCID 54529925HCID 54529925、化合物収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl-1,2,3,4,4a,-5,6,10b-octahydrobenzo[f]quinolin-3-one (50 mg, 0.16 mmol), N,N-dimethylaminopyridine (3 mg, 0.024 mmol), benzoic acid (21 mg, 0.18 mmol), and 0.4 mL of dichloromethane. 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (EDCI) hydrochloride (120 mg, 0.64 mmol) was added in one portion, and the mixture was stirred at room temperature for 10 min. The mixture was diluted with dichloromethane, and the organic phase was washed with water followed by brine. The organic phase was dried over sodium sulfate, concentrated, and chromatographed on silica gel (0-50% methanol/ethyl acetate eluent gradient) to give 50 mg (76%) of the title compound as an amorphous foam. mp 257°-262° (decomp.) FDMS m/e=424. α[D]589 =+62.50 (c=0.61, chloroform).

後処理

  1. washthe organic phase was washed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customchromatographed on silica gel (0-50% methanol/ethyl acetate eluent gradient)

出典と根拠

ORDレコード
ord-d1f06d29d6004840803ab704084b6d97
出典データセット
uspto-grants-1997_09
特許番号
US05670514

反応ノート

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