Trifluoroacetic acid → HCID 59692121, compound

HRID 898356Notes

Reaction equation

HRID 898356 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH2:20][CH:21]([OH:40])[CH:22]([NH:32]C(OC(C)(C)C)=O)[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:32][C@@H:22]([CH2:23][C:24]1[CH:25]=[C:26]([F:31])[CH:27]=[C:28]([F:30])[CH:29]=1)[C@H:21]([OH:40])[CH2:20][N:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:9](=[O:41])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69195805HCID 69195805, compound

Product 1

HCID 59692121HCID 59692121, compound

Procedure

To a 20 ml solution of [3-tert-butoxycarbonylamino-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxybenzyl)-carbamic acid benzyl ester (0.5 g, 0.9 mmol) at 0° C. was added trifluoroacetic acid (4 ml). The cold bath was removed and the mixture stirred at r.t. for 1 h. The solvent was removed in vacuo and the residue dissolved in 10% aq. NaHCO3, extracted with EtOAc (3×115 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to yield an amorphous solid. MS (ESI+) for C26H28F2N2O4 m/z 471.2 (M+H)+. The crude amine was used in subsequent steps without purification.

Workup

  1. customThe cold bath was removed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in 10% aq. NaHCO3
  4. extractionextracted with EtOAc (3×115 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto yield an amorphous solid
  8. customThe crude amine was used in subsequent steps without purification

Sources & evidence

ORD record
ord-4eefb46c60954485b636081d800e0473
Source dataset
uspto-grants-2008_04
Patent number
US07351738B2

Reaction notes

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