Oxalic 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 oxalate

HRID 239091

Reaction equation

HRID 239091 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]([OH:52])(=[O:51])[C:48]([OH:50])=[O:49]>C(OCC)(=O)C>[C:47]([OH:52])(=[O:51])[C:48]([OH:50])=[O: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]

Participants

5

Reactant 3

HCID 971Oxalic 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 68227660(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To ethyl acetate (5 mL) solution containing 251.0 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): 171.5 mg and (8a): 75.1 mg], 67.7 mg (content: 98 wt %) of oxalic acid was added and stirred for 17 hrs and 50 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. 217.0 mg of the resulting colorless powder (229.1 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 193.5 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluorobicyclo[3.1.0]hexane-6-carboxamide oxalate (6d) 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-e89087b9ecd44e4485861a175069ea7a
Source dataset
uspto-grants-2014_02
Patent number
US08642777B2

Linked notes

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