Trifluoroacetic acid → methyl (2S)-2-amino-3-(4-{[(isopropylamino)carbonyl]oxy}phenyl)propanoate

HRID 449473Notes

Reaction equation

HRID 449473 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C@@H:16]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29](=[O:34])[NH:30][CH:31]([CH3:33])[CH3:32])=[CH:24][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=O)(C)(C)C>C(Cl)Cl>[NH2:15][C@@H:16]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:34])=[CH:24][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59496584(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate

Product 1

HCID 59496562methyl (2S)-2-amino-3-(4-{[(isopropylamino)carbonyl]oxy}phenyl)propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 6 mmol) was added to (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate in methylene chloride (2 mL). The reaction was stirred for 1 h, and was concentrated under reduced pressure to give crude product, methyl (2S)-2-amino-3-(4-{[(isopropylamino)carbonyl]oxy}phenyl)propanoate (50 mg, 100%). Analytical LCMS (M+H)+: m/z=281.0.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e91785f37de4f9192ec201e6d2d28a5
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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