Trifluoroacetic acid → (R)-2-Amino-4-(4-heptyloxy-phenyl)-2-methyl-butanoic acid

HRID 12585

Reaction equation

HRID 12585 reaction equation
C(OC([NH:8][C@:9]([CH3:29])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@:9]([CH3:29])([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:20]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58897679(R)-2-tert-butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid

Product 1

HCID 11404040(R)-2-Amino-4-(4-heptyloxy-phenyl)-2-methyl-butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-2-tert-butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid (43 mg, 0.11 mMol) in CH2Cl2 (2 ml) is added trifluoroacetic acid (0.1 ml). The mixture is stirred at RT for 8 hours. After that time, the reaction mixture is concentrated under reduced pressure. Column chromatography eluting with 5%→25% MeOH in CH2Cl2 gives the title compound as a colourless oil.

Workup

  1. concentrationAfter that time, the reaction mixture is concentrated under reduced pressure
  2. washColumn chromatography eluting with 5%→25% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-dc96f4ef043c40f5b91e8bb96a45a857
Source dataset
uspto-grants-2010_06
Patent number
US07728020B2

Linked notes

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