Trifluoroacetic acid → Trifluoroacetic acid

HRID 1014944Notes

Reaction equation

HRID 1014944 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:34]#[N:35])([NH:14][C:15]([O:17][C@@H:18]([CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(Cl)Cl>[C:34]([C:11]1([NH:14][C:15]([O:17][C@@H:18]([CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:19]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:20])=[O:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)#[N:35].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58458966HCID 58458966, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67300943HCID 67300943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sample of the title compound of Example 6 (125 mg, 0.254 mmol) is dissolved in DCM (1 mL) and TFA (1 mL). The reaction is allowed to stir for 1 hour and the volatiles are removed by rotary evaporation to afford pure (S)-4-cyano-4-(1-cyclohexylmethyl-2-morpholin-4-yl-2-oxo-ethoxycarbonylamino)-piperidine in quantitative yield as TFA salt. The corresponding free amine is prepared by addition of 1M NaOH and extraction into DCM followed by drying and rotary evaporation of the organic layer. HPLC-MS calculated for C20H32N4O4 (M+H+) 393.2, found 393.3.

Workup

  1. customthe volatiles are removed by rotary evaporation

Sources & evidence

ORD record
ord-3fcac1a70a3e4973b88d153161fe5b85
Source dataset
uspto-grants-2011_07
Patent number
US07985749B2

Reaction notes

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