Acetic Acid → HCID 86645984, compound

HRID 1094331Notes

Reaction equation

HRID 1094331 reaction equation
[C-]#[N:2].[K+].O.[NH:5]1[C:9]([C@@H:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=3)=[CH:14][CH:13]=2)[CH3:11])=[CH:8]C=N1.C([O-])(=O)CC.CC(O)=O.[NH4+].[Cl-].[NH4+].[OH-]>>[NH2:5][CH:9]([C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=2)=[CH:14][CH:13]=1)[CH3:11])[C:8]#[N:2]

Participants

8

Reactant 7

HCID 176Acetic AcidHCID 962WaterHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 104745Propionate ionHCID 86645974HCID 86645974, compound

Product 1

HCID 86645984HCID 86645984, compound

Procedure

To a cooled (0-5° C.) solution of potassium cyanide (0.2 g, 3.66 mmol) in water (15 ml) (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanal (1.0 g, 3.33 mmol) (prepared according the procedure described for intermediate 7b and starting from the corresponding propanoate) was added over 30 min. At the same temperature AcOH (3.66 mmol) was dripped and the reaction mixture stirred for 18 h. The solution of the intermediate cyanohydrin was slowly added to another solution of NH4Cl (0.5 g, 9.66 mmol) in NH4OH (14N in H2O; 4.0 mmol) (5 ml). The resulting reaction mixture was stirred at room temperature for 18 h and then extracted with CH2Cl2 (3×15 ml). The organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum to give (3R)-2-amino-3-{4-[(4-(trifluoromethyl)-1,3-thiazol-2-yl)amino]phenyl}butanenitrile (0.705 g, 2.16 mmol) as red oil, used for the next step without further purification. 1H-NMR (DMSO-d6): δ 9.25 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.00 (s, 1H), 5.00 (s, 1H), 3.90 (q, 1H, J=7 Hz), 2.35 (bs, 2H), 1.75 (d, 3H, J=7 Hz).

Workup

  1. customprepared
  2. additionwas added over 30 min
  3. customThe resulting reaction mixture
  4. stirringwas stirred at room temperature for 18 h
  5. extractionextracted with CH2Cl2 (3×15 ml)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-19c928f035d1404fb18b169768d1eed3
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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