Trifluoroacetic acid → (2R)-2-[(2R)-4-(4-aminophenyl)-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamide

HRID 876572Notes

Reaction equation

HRID 876572 reaction equation
[C:1]([C:3]1[CH:34]=[CH:33][C:6]([NH:7][C:8](=[O:32])[C@@H:9]([C@H:11]2[O:16][CH2:15][CH2:14][N:13]([C:17]3[CH:22]=[CH:21][C:20]([NH:23]C(=O)OC(C)(C)C)=[CH:19][CH:18]=3)[C:12]2=[O:31])[OH:10])=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>CCOCC>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:13]2[CH2:14][CH2:15][O:16][C@H:11]([C@@H:9]([OH:10])[C:8]([NH:7][C:6]3[CH:33]=[CH:34][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[O:32])[C:12]2=[O:31])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 67222096tert-butyl N-[4-[(2R)-2-[(1R)-2-(4-cyanoanilino)-1-hydroxy-2-oxoethyl]-3-oxomorpholin-4-yl]phenyl]carbamate

Product 1

HCID 67032877(2R)-2-[(2R)-4-(4-aminophenyl)-3-oxomorpholin-2-yl]-N-(4-cyanophenyl)-2-hydroxyacetamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To compound 26-4 (1.65 g), was added trifluoroacetic acid (10 mL) with anisole (0.2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour then Et2O was added into the mixture to precipitate. The precipitate was collected by filtration and washed with Et2O. Then the precipitate was solved in water and the solution was basified with sat. NaHCO3 aq. The precipitate was collected by filtration and washed with H2O to obtain compound 26-5 (1.2 g) as a pale brown amorphous solid.

Workup

  1. customto precipitate
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with Et2O
  4. filtrationwas collected by filtration
  5. washwashed with H2O

Sources & evidence

ORD record
ord-c4f3107153b349db8beab8280952077f
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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