Methyl chloroformate → HCID 69803216, compound

HRID 488672Notes

Reaction equation

HRID 488672 reaction equation
[CH:1]1[C:6]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([N+:13]([O-:15])=[O:14])[CH:2]=1.[OH-].[Na+].[CH3:18][O:19][C:20](Cl)=[O:21]>O>[CH3:18][O:19][C:20]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[CH:2][CH:1]=1)=[O:21]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 137064-Nitro-3-phenyl-L-alanineHCID 14798Sodium Hydroxide4×

Product 1

HCID 69803216HCID 69803216, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of H-phe(4-NO2)-OH (11.4 g, 50.0 mmol) and NaOH (2.0 g, 50.0 mmol) in water (450 mL) at 0° C. was added methylchloroformate (4.25 mL, 55.0 mmol) and NaOH (2.2 g in 45 mL water) simultaneously. 1N NaOH was then added to adjust PH ˜9. The reaction mixture was stirred at ambient temperature overnight, the pH was adjust to 10 by adding more aqueous NaOH and the mixture was extracted with ether (2×75 mL). The aqueous layer was acidified to a pH=3 with 5N HCl, and extracted with ethyl acetate (2×400 mL). The combined ethyl acetate layers were dried (MgSO4), filtered and concentrated under reduced pressure to provide the titled compound (12.3 g). MS (ESI (−)) m/e 267 (M−H)+; 1H NMR (300 MHz, DMSO-d6) 8.16 (d, 2H), 7.60-7.52 (m, 3H), 4.28-4.18 (m, 1H), 3.47 (s, 3H), 3.26-3.17 (m, 1H), 3.05-2.92 (m, 1H).

Workup

  1. extractionthe mixture was extracted with ether (2×75 mL)
  2. extractionextracted with ethyl acetate (2×400 mL)
  3. dry with materialThe combined ethyl acetate layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-364255ab3f064eb38dae59f30433945d
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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