HCID 66988011, compound → HCID 66987921, compound

HRID 333436Notes

Reaction equation

HRID 333436 reaction equation
C(OC([NH:8][C@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:8][C@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][C:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11]

Participants

4

Reactant 1

HCID 66988011HCID 66988011, compound

Product 1

HCID 66987921HCID 66987921, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.26 g (0.5 mmol) of ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(4-chlorophenyl)-propionyl]-4-cyclohexylpiperidine-4-carboxylate is diluted in 4 mL of DCM and 1 mL of trifluoroacetic acid, and the solution is stirred for 2 hours at room temperature and then quenched by adding aqueous 1N NaOH solution and extracted with dichloromethane. The organic phase is dried and then evaporated. 200 mg of ethyl 1-[(R)-2-amino-3-(4-chlorophenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate in the form of a colourless oil are obtained in a yield of 95%.

Workup

  1. customquenched
  2. additionby adding aqueous 1N NaOH solution
  3. extractionextracted with dichloromethane
  4. customThe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-2269b33abfe341ee8b21bdb8e0b686aa
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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