Trifluoroacetic acid → HCID 57554905, compound

HRID 1941776Notes

Reaction equation

HRID 1941776 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][N:14]([CH2:28][CH3:29])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH2:28]([N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)[CH2:13][C@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[CH3:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68727908HCID 68727908, compound

Product 1

HCID 57554905HCID 57554905, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-{[ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.162 g, 0.41 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (1 ml) and the mixture was stirred for 3 h at room temperature. Aqueous sodium hydroxide solution (4N) was added until basic pH and the mixture was extracted with ethyl acetate (2 times 30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate) to yield a colourless oil, (0.043 g, 36%); MS (ISP): 297.5 ((M+H)+.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2 times 30 ml)
  2. dry with materialThe combined organic layers were dried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate)
  6. customto yield a colourless oil, (0.043 g, 36%)

Sources & evidence

ORD record
ord-cebedf7b323f49ceb71108f4b7718ac7
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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