Methyl iodide → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate

HRID 63714Notes

Reaction equation

HRID 63714 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH3:23][O:13][C:12](=[O:14])[C@@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 11558856(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid (70.2 g, 226.2 mmol) and sodium carbonate (95 g, 1.13 mole) in DMF (500 mL) was added methyl iodide (70.4 mL, 1.13 mole) at room temperature. The suspension was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material and the excess methyl iodide and some DMF were removed under high vacuum. Then, it was poured into water (2 L) and stirred at room temperature as a precipitate formed slowly over 72 h. The precipitated solids were collected by filtration and washed with water (2 L). After air and vacuum drying, 72 g (98% yield) of (S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester was isolated as a light yellow solid (mp 95-96° C.). ES(+)-HRMS m/e calcd. for C15H20N2O6 (M+H)+ 325.1400, obsd. 325.1404.

Workup

  1. customthe excess methyl iodide and some DMF were removed under high vacuum
  2. additionThen, it was poured into water (2 L)
  3. stirringstirred at room temperature as a precipitate
  4. customformed slowly over 72 h
  5. filtrationThe precipitated solids were collected by filtration
  6. washwashed with water (2 L)
  7. customAfter air and vacuum drying

Sources & evidence

ORD record
ord-899fbaba7a054a3e864b7b56d43c94f4
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

Loading…