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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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p-Toluenesulfonic acid → (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide p-toluene sulfonate

HRID 239092
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HRID 239092 반응식
[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18]([NH2:20])=[O:19].N[C@]1(C#N)[C@H](OCC2C=CC(Cl)=C(Cl)C=2)C[C@@H]2[C@H]1[C@@]2(F)C(N)=O.[C:47]1([CH3:57])[CH:52]=[CH:51][C:50]([S:53]([OH:56])(=[O:55])=[O:54])=[CH:49][CH:48]=1>C(OCC)(=O)C>[C:47]1([CH3:57])[CH:48]=[CH:49][C:50]([S:53]([OH:56])(=[O:54])=[O:55])=[CH:51][CH:52]=1.[NH2:1][C@@:2]1([C:22]#[N:23])[C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:6][C@@H:5]2[C@H:3]1[C@@:4]2([F:21])[C:18]([NH2:20])=[O:19]
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참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 53236629(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamideHCID 68227672(1R,2R,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide

생성물 1

HCID 86671128(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide p-toluene sulfonate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To ethyl acetate (5 mL) solution containing 251.7 mg of the mixture of ((1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (6a) and (1R,2R,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (8a) [containing (6a): 172.0 mg and (8a): 75.3 mg], 139.4 mg (content: 98 wt %) of p-toluene sulfonic acid was added and stirred for 18 hrs and 20 min at room temperature. The resulting slurry was filtered under suction, washed with 2 mL of ethyl acetate, and dried under reduced pressure at room temperature. 233.2 mg of the resulting colorless powder (248.0 mg obtained) was suspended in 2.5 mL of ethyl acetate, and stirred at room temperature for 15.5 hrs. The resulting slurry was filtered under suction, washed with 2 mL of ethyl acetate, and dried under reduced pressure at room temperature to obtain 220.6 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide p-toluene sulfonate (6e) as a colorless solid.

후처리

  1. additionwas added
  2. filtrationThe resulting slurry was filtered under suction
  3. washwashed with 2 mL of ethyl acetate
  4. customdried under reduced pressure at room temperature
  5. stirringstirred at room temperature for 15.5 hrs
  6. filtrationThe resulting slurry was filtered under suction
  7. washwashed with 2 mL of ethyl acetate
  8. customdried under reduced pressure at room temperature

출처 및 근거

ORD 기록
ord-dd38d221460e4949bf6e74a37ed95665
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642777B2

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