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Hydrochloric Acid → HCID 53357878、化合物

HRID 1807294
ノート
印刷プレビュー

反応式

HRID 1807294 の反応式
[Cl:1][C:2]1[C:3]([F:44])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:32]=[CH:33][C:34]3[O:38][C:37]([C:39]([O:41]C)=[O:40])=[N:36][C:35]=3[CH:43]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:1][C:2]1[C:3]([F:44])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:25])[CH3:26])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:32]=[CH:33][C:34]3[O:38][C:37]([C:39]([OH:41])=[O:40])=[N:36][C:35]=3[CH:43]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53357877HCID 53357877、化合物

生成物 1

HCID 53357878HCID 53357878、化合物収率 12.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran
溶媒

実験手順

A solution of chiral methyl 5-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)benzo[d]oxazole-2-carboxylate (64.5 mg, 0.101 mμmol) in THF (5 ml) was reacted with LITHIUM HYDROXIDE MONOHYDRATE (17.1 mg, 0.407 mmol) in water (2.5 ml) and stirred at rt for 4.5 hrs. The reaction mixture was treated with 1 N HCl (pH 5-6) and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried with sodium sulfate, filtered and purified by silica gel chromatography with methylene chloride and methanol to give chiral-5-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)benzo[d]oxazole-2-carboxylic acid (7.8 mg., 12.4%) a white lyophilized solid. MS (ES+) m/z Calcd: [(M+H)+]: 627.13. found: 627.2. and chiral (2R,3S,4R,5S)—N-(benzo[d]oxazol-5-yl)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamide (38.3 mg., 65.3%) as a white lyophilized solid. MS (ES+) m/z Calcd: [(M+H)+]: 583.14. found: 583.2.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. custompurified by silica gel chromatography with methylene chloride and methanol

出典と根拠

ORDレコード
ord-8f90efb32282443498aa17db900d2289
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354444B2

反応ノート

読み込み中…

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