Hydrochloric Acid → (R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid

HRID 1530765Notes

Reaction equation

HRID 1530765 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17].Cl>O.O1CCCC1>[CH3:19][O:18][C:16]([NH:1][C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformate2×HCID 14798Sodium Hydroxide2×HCID 71567D-Phenylalanine

Product 1

HCID 10799103(R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of D-phenylalanine (I, 25.00 g, 0.151 mol) and sodium hydroxide (6.05 g, 0.151 mol) in water (170 ml) and tetrahydrofuran (225 ml) is cooled to −15°, and a mixture of methyl chloroformate (18.6 g, 0.197 mol) in tetrahydrofuran (50 ml) is added dropwise. When the one-half of the methyl chloroformate had been added, a mixture of sodium hydroxide (9.10 g, 0.227 mol) in water (20 ml) is added. When the addition is complete, the mixture is stirred at 25° for an additional 2 hours and acidified with hydrochloric acid (10%) to pH 2. The mixture is extracted twice with ether and the extracts are washed with saline and dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound, NMR (CDCl3) 3.09, 3.19, 3.65, 4.66, 5.25, 7.15-7.31 and 8.22 δ; IR (thin film) 1726, 1498, 1455, 1448 and 1377 cm−1; MS calculated for C11H13NO4=224.0923, found=224.0921.

Workup

  1. temperatureis cooled to −15°
  2. additionis added dropwise
  3. additionis added
  4. additionWhen the addition
  5. extractionThe mixture is extracted twice with ether
  6. washthe extracts are washed with saline
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-4b5e272acd4d4a5a97511b5793680da9
Source dataset
uspto-grants-2001_03
Patent number
US06197339B1

Reaction notes

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