Methyl iodide → HCID 22940672, compound

HRID 860174Notes

Reaction equation

HRID 860174 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-butoxycarbonylamino]-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 RT 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-7a805e2d4cdc4652bcbe0917c3d01533
Source dataset
uspto-grants-2006_12
Patent number
US07153868B2

Reaction notes

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