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Acetic Acid → (1S,2R)-5'-(4-chlorophenyl)-2-(methoxymethyl)-6',7'-dimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

HRID 1772333
ノート
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反応式

HRID 1772333 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=O.C1(C(=[N:31][C@@:32]2([C:38](OCC)=[O:39])[CH2:34][C@H:33]2[CH2:35][O:36][CH3:37])C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].C(O)(=O)C>C1COCC1.C(O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:6]3[C:5]([CH3:16])=[C:4]([CH3:17])[S:3][C:2]=3[NH:1][C:38](=[O:39])[C@@:32]3([CH2:34][C@H:33]3[CH2:35][O:36][CH3:37])[N:31]=2)=[CH:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanoneHCID 23665647Potassium tert-butoxideHCID 86706920(1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-(methoxymethyl)cyclopropanecarboxylate

生成物 1

HCID 136338064(1S,2R)-5'-(4-chlorophenyl)-2-(methoxymethyl)-6',7'-dimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (7.09 g, 26.7 mmol) and (1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-(methoxymethyl)cyclopropanecarboxylate (6 g, 17.78 mmol) in anhydrous THF (100 mL) was slowly (over 5 min) added a solution of potassium tert-butoxide (1 M in THF) at rt. The reaction was heated to 60° C. for approximately 20 h before acetic acid (10.68 g, 178 mmol) and absolute ethanol (20 mL) were added at 60° C. THF was distilled off, and the reaction was heated to reflux for 3 h. The reaction was cooled to rt before silica gel was added, and the solvent was removed under vacuum. The dry silica gel was packed and the product was purified by flash chromatography (EtOAc/hexane 1:19 to 6:14) to give (1S,2R)-5′-(4-chlorophenyl)-2-(methoxymethyl)-6′,7′-dimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one a solid (3.7 g). LRMS (M+H)+: 375 m/z.

後処理

  1. custom(over 5 min)
  2. additionwere added at 60° C
  3. distillationTHF was distilled off
  4. temperaturethe reaction was heated
  5. temperatureto reflux for 3 h
  6. additionwas added
  7. customthe solvent was removed under vacuum
  8. customthe product was purified by flash chromatography (EtOAc/hexane 1:19 to 6:14)

出典と根拠

ORDレコード
ord-42b200e45a4d42a6bf1ac9e82aa1c07c
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249161B2

反応ノート

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