Trifluoroacetic acid → (R)-2-Amino-N-benzyl-3-methoxypropionamide

HRID 587410Notes

Reaction equation

HRID 587410 reaction equation
[CH2:1]([NH:8][C:9](=[O:22])[C@@:10]([NH2:21])(C(OC(C)(C)C)=O)[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:21][C@H:10]([CH2:11][O:12][CH3:13])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67142327HCID 67142327, compound

Product 1

HCID 10104501(R)-2-Amino-N-benzyl-3-methoxypropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)—N-benzyl-2-Boc-amino-3-methoxypropanamide (9.8 g, 31.8 mmol) was dissolved in 15 mL of DCM and then 15 mL of TFA was added to the solution. The mixture was stirred at room temperature for two hours. The solvent and TFA was removed by evaporation and a white solid was obtained (12.4, 100%). Upon analysis, it was determined that on average each molecule contained 1.6 TFA. 1H NMR (500 MHz, DMSO) δ 3.30 (s, 3H), 3.69 (m, 2H), 4.05 (m, 1H), 4.35 (m, 2H), 7.25 (m, 3H), 7.35 (m, 2H), 8.23 (br., 2H), 8.95 (m, 1H). LC-MS (m/z) calcd. 208.1. Found 209.1 [M+H]+.

Workup

  1. customThe solvent and TFA was removed by evaporation
  2. customa white solid was obtained (12.4, 100%)

Sources & evidence

ORD record
ord-46a4cd05fd73479589bc57cb7274fda1
Source dataset
uspto-grants-2016_01
Patent number
US09226971B2

Reaction notes

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