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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
Notes
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Reaction equation

HRID 239092 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dd38d221460e4949bf6e74a37ed95665
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642777B2

Reaction notes

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