Cyclopentylacetic acid → HCID 86714411、化合物

HRID 1750198ノート

反応式

HRID 1750198 の反応式
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[C:34]([NH2:44])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:40][CH3:41])[CH2:42][CH3:43])=[C:34]([NH:44][C:7](=[O:9])[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:33]=1

参加物

8

反応物 4

HCID 71606Cyclopentylacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2 回HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

生成物 1

HCID 86714411HCID 86714411、化合物収率 73%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 16.41 g of cyclopentyl-acetic acid in 600 ml of dry DMF 17.30 g of HOBT, 24.54 g of EDC and 30 ml of DIPEA were added at 0° C. After 1 h 27.51 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 30 ml of DIPEA were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by crystallization from diisopropylether to yield 29.35 g (73%) of 3-(2-cyclopentyl-acetylamino)-4-(1-ethyl-propylamino)-benzoic acid methyl ester as an off-white solid.

後処理

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by crystallization from diisopropylether

出典と根拠

ORDレコード
ord-1567141a3c60491ca2bdef57e9697e97
出典データセット
uspto-grants-2015_10
特許番号
US09156796B2

反応ノート

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