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Hydrochloric Acid → (S)-1-((R)-2-Hydroxy-3,3-dimethyl-butyryl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide

HRID 1058279
ノート
印刷プレビュー

反応式

HRID 1058279 の反応式
[CH3:1][C:2]([CH3:33])([CH3:32])[C@@H:3]([OH:31])[C:4]([N:6]1[CH2:30][CH2:29][CH2:28][C@H:7]1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH2:19][NH:20]C(OC(C)(C)C)=O)=[O:9])=[O:5].Cl>C(Cl)Cl.CCOCC>[CH3:1][C:2]([CH3:33])([CH3:32])[C@@H:3]([OH:31])[C:4]([N:6]1[CH2:30][CH2:29][CH2:28][C@H:7]1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[CH2:19][NH2:20])=[O:9])=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 113061991-((2R)-3,3-dimethyl-2-hydroxybutanoyl)-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide

生成物 1

HCID 11740591(S)-1-((R)-2-Hydroxy-3,3-dimethyl-butyryl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

1-((2R)-3,3-Dimethyl-2-hydroxybutanoyl)-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide from the previous step (4.65 g, 9.65 mmol, HPLC RT=3.35 min) was dissolved in CH2Cl2 (15 mL) and cooled with stirring to 0° C. A solution of anhydrous HCl in ether (38 mL of a 1 Molar solution, 38 mmol) was added slowly. The resulting solution was stirred at 0° C. for 10 min, and then at ambient temperature for 20 h. The solid which had formed was collected by filtration and washed with several portions of ether. The solid was purified by preparative reverse-phase HPLC using an acetonitrile:water gradient containing 0.05% concentrated HCl. The product-containing fractions were combined and lyophilized to give the hydrochloride salt of the title compound as a white solid (HPLC RT=2.52 min, method A; LC-MS m/z=382; C, H, N combustion analysis, calculated for C19H28ClN3O3, 1.0HCl, 1.5H2O, calculated C, 51.24, H, 7.24, N, 9.43, found C, 51.32, H, 7.17, B, 9.33).

後処理

  1. temperaturecooled
  2. stirringThe resulting solution was stirred at 0° C. for 10 min
  3. customThe solid which had formed
  4. filtrationwas collected by filtration
  5. washwashed with several portions of ether
  6. customThe solid was purified by preparative reverse-phase
  7. additionwater gradient containing 0.05% concentrated HCl

出典と根拠

ORDレコード
ord-f949b0d351d94e6f863acd00f6d3537a
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06515011B2

反応ノート

読み込み中…

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