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

HRID 47149

Reaction equation

HRID 47149 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 chloroformateHCID 14798Sodium Hydroxide2×HCID 71567D-Phenylalanine

Product 1

HCID 10799103(R)-2-(methoxycarbonylamino)-3-phenylpropanoic acidYield 113.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of D-phenylalanine (25.00 g, 0.151 mol) and sodium hydroxide (6.05 g, 0.151 mol) in water (170 ml) and tetrahydrofuran (225 ml) was cooled to −15° C., and a solution of methyl chloroformate (18.6 g, 0.197 mol) in tetrahydrofuran (50 ml) was added dropwise. When the addition was ˜half complete, a solution of sodium hydroxide (9.10 g, 0.227 mol) in water (20 ml) was also added dropwise. When the additions were complete, the mixture was stirred at room temperature for an additional 2 hours and acid fixed with 10% hydrochloric acid. The acid was extracted twice with diethylether, and the extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a clear oil (38.38 g). HPLC 6.01 min (78.9%), 7.32 min (5.0%), 8.29 min (10.8%), 8.42 min (0.5%), 9.95 min (1.2%), 10.27 min (2.8%), 11.92 min (0.7%).

Workup

  1. additionWhen the addition
  2. additionwas also added dropwise
  3. extractionThe acid was extracted twice with diethylether
  4. washthe extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a3c6958a412c4737b0184493e43e5a7a
Source dataset
uspto-grants-2004_03
Patent number
USRE038452E1

Linked notes

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