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

HRID 901812Notes

Reaction equation

HRID 901812 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 113,863.602%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of D-phenylalanine (25.00 g, 0.151 mmol) 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. extractionThe acid was extracted twice with diethylether
  3. washthe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ca823e99bc2c4e90998c59e3ccc7c776
Source dataset
uspto-grants-2008_04
Patent number
USRE040278E1

Reaction notes

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