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Hydrochloric Acid → Tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylate

HRID 1892540
ノート
印刷プレビュー

反応式

HRID 1892540 の反応式
[SH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[NH:34][NH2:35].Cl>O1CCCC1.C(OCC)(=O)C.O>[C:18]([NH:17][C:14]1[S:15][CH:16]=[C:12]([CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][S:1][C:21]([NH:35][NH:34][C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:22])=[CH:5][CH:6]=2)[N:13]=1)(=[O:20])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazateHCID 86650044N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

生成物 1

HCID 86650045Tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylate収率 84.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-(4-{2-[4-(2-sulfanylethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (368.0 mg, 1.201 mmol) in anhydrous tetrahydrofuran (30 ml) was added 1,1′-carbonyldiimidazole (291.4 mg, 1.797 mmol), and the mixture was stirred at room temperature for 1 hr. tert-Butyl carbazate (477.9 mg, 3.616 mmol), anhydrous tetrahydrofuran (2 ml) was added, and the mixture was stirred at room temperature for 19 hr. Water (20 ml), 1M hydrochloric acid (10 ml) and ethyl acetate (30 ml) were added, and the mixture was stirred, stood still and partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=1:1) to give tert-butyl 2-({[2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethyl]sulfanyl}carbonyl)hydrazinecarboxylate (469.9 mg, 1.011 mmol, yield 84.2%) as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 19 hr
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-6a63d2ca773f43dabea3e2467e253827
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507690B2

反応ノート

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