L-Tartaric 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 L-tartarate

HRID 239090

反応式

HRID 239090 の反応式
[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]([OH:56])(=[O:55])[C@@H:48]([C@H:50]([C:52]([OH:54])=[O:53])[OH:51])[OH:49]>C(OCC)(=O)C>[C:47]([OH:56])(=[O:55])[C@@H:48]([C@H:50]([C:52]([OH:54])=[O:53])[OH:51])[OH:49].[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]

参加物

5

反応物 3

HCID 444305L-Tartaric 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

生成物 1

HCID 86671127(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide L-tartarate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To ethyl acetate (5 mL) solution containing 250.2 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): 168.6 mg and (8a): 74.8 mg], 107.9 mg (content: 99 wt %) of L-tartaric acid was added and stirred for 19 hrs and 15 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. 254.6 mg of the resulting colorless powder (265.9 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 206.9 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 L-tartarate (6c) as a colorless solid.

後処理

  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

出典と根拠

ORDレコード
ord-7420fd1ed9f341bc980b528f802d42ac
出典データセット
uspto-grants-2014_02
特許番号
US08642777B2

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