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Hydrochloric Acid → Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

HRID 1746626
ノート
印刷プレビュー

反応式

HRID 1746626 の反応式
C(N(CC)CC)C.CS(C)=O.[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13].Cl>C(OCC)(=O)C>[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13]
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 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 15979344Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

生成物 1

HCID 86634273Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate収率 99.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (3.7 mL) and sulfur trioxide•pyridine complex (1.7 g) were added to a dimethyl sulfoxide(4.0 mL)/ethyl acetate(8.0 mL) solution of ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate (500 mg) (see compound 7 described in the pamphlet of International Publication No. WO 2006/129788) at 10° C., followed by stirring at room temperature for 30 min. To the reaction solution, 1 N hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine; dried with anhydrous sodium sulfate; and concentrated to obtain the title compound (497 mg) having the following physical properties:

後処理

  1. customat 10° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationand concentrated

出典と根拠

ORDレコード
ord-dbef88a1017f48afa9028958767345c4
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150528B2

反応ノート

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