Trifluoroacetic acid → methyl (2S)-2-amino-3-(4-isopropoxyphenyl)propanoate

HRID 449470Notes

Reaction equation

HRID 449470 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][CH:29]([CH3:31])[CH3:30])=[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:23]=[CH:24][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59496538(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate

Product 1

HCID 59496671methyl (2S)-2-amino-3-(4-isopropoxyphenyl)propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 6 mmol) was added to the (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate in methylene chloride (2 mL). The reaction was stirred for 1 h., and was concentrated under reduced pressure to give a crude product, methyl (2S)-2-amino-3-(4-isopropoxyphenyl)propanoate (40 mg, 100%) as colorless oil. Analytical LCMS (M+H)+: m/z=238.0.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-55c6b53354c84e3fa698d72a813fa617
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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