Trifluoroacetic acid → (S)-Ethyl 2-(N-(5-amino-1-phenylpentan-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate

HRID 1429410Notes

Reaction equation

HRID 1429410 reaction equation
[C:1](/[CH:3]=[CH:4]/[C@H:5]([N:13]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>CO.O=[Pt]=O.[Pt]>[NH2:2][CH2:1][CH2:3][CH2:4][C@H:5]([N:13]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:26])([F:27])[F:25])(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71277869(R,E)-Ethyl 2-(N-(4-cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate

Product 1

HCID 71277454(S)-Ethyl 2-(N-(5-amino-1-phenylpentan-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 31h (3.7 g, 7.7 mmol) in MeOH (200 mL) were added PtO2 (0.1 g), Pt/C (0.3 g) and TFA (1.9 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 12 h. The mixture was filtered and concentrated. The product was directly used in the next reaction step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe product was directly used in the next reaction step without further purification

Sources & evidence

ORD record
ord-9ef68e43c63946d689288ba4f52207e5
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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