Hydrochloric Acid → 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester

HRID 1750231ノート

反応式

HRID 1750231 の反応式
[S:1]1[C:5]([CH2:6][C:7]([OH:9])=O)=[CH:4][N:3]=[CH:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[CH3:45])=[C:34]([NH2:46])[CH:33]=1.Cl>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[CH3:45])=[C:34]([NH:46][C:7](=[O:9])[CH2:6][C:5]2[S:1][CH:2]=[N:3][CH:4]=2)[CH:33]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2 回HCID 181649HOAtHCID 3494395-Thiazoleacetic acidHCID 867144383-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester

生成物 1

HCID 867144394-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester収率 94.2%

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 0.49 g of thiazol-5-yl-acetic acid in 10 ml of dry DMF 0.27 g of HOAT, 0.79 g of EDC and 1 ml of DIPEA were added at 0° C. After 30 min 0.9 g of 3-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester were added, followed by the addition of 1 ml of DIPEA and the reaction was stirred at it for 48 h. The reaction was then poured into water, brought to pH3 by the addition of 2 M aqueous hydrochloric acid 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 to obtain 1.25 g (94%) of 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiazol-5-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

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

出典と根拠

ORDレコード
ord-af0b6516e9d34932a841b7534eb9a1bc
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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