Methyl iodide → HCID 22940672, compound

HRID 1635950Notes

Reaction equation

HRID 1635950 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:22]([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:10][C:11]([O:13][CH3:22])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2734490(3S)-3-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoic acid

Product 1

HCID 22940672HCID 22940672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 15 mL of DMF charged with (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionic acid (8 mmol, 2.0 g), methyl iodide (15 mmol, 1.9 mL) and K2CO3 (15 mmol, 2.1 g), was stirred at ambient temperature for 16 h. The reaction mixture was poured into 50 mL of saturated NaHCO3, and the resulting solution was extracted with ether (3×50 mL). The combined organic phase was washed with 50 mL of H2O, dried with MgSO4, and the solvent removed under reduced pressure to yield the title compound as a slightly yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.26-7.38 (m, 5 H), 5.49 (br s, 1H), 5.13 (br s, 1H), 3.65 (s, 3H), 2.80-2.96 (m, 2H), 1.45 (s, 9H). MS (ESI): m/z 302 (M+Na).

Workup

  1. extractionthe resulting solution was extracted with ether (3×50 mL)
  2. washThe combined organic phase was washed with 50 mL of H2O
  3. dry with materialdried with MgSO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-207ac9a976c74546a791a0d38c9e2a98
Source dataset
uspto-grants-2003_01
Patent number
US06511994B2

Reaction notes

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