Hydrochloric Acid → (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid

HRID 714129Notes

Reaction equation

HRID 714129 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].Cl[C:19]([O:21][CH3:22])=[O:20].Cl>C1COCC1>[CH3:22][O:21][C:19]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidYield 198.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of L-diphenylalanine (13.87 g, 57.5 mmol) in THF (100 ml), and saturated NaHCO3 (3 mL) stirred at 0° C. was treated with neat methyl chloroformate (11.81 g, 125 mmol) (slow addition), stirred at the same temperature for 10 min and then at room temperature for 14 h, made acidic by addition of 1M HCl and extracted with DCM, dried over MgSO4 filtered and concentrated to give title compound (17.1 g, 99% yield) as white solid. Used without further purification. MS: m/z=322.1 (MNa+).

Workup

  1. stirringstirred at the same temperature for 10 min
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1920437b70054c55954a76cd97adb72e
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

Loading…