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

HRID 266689

Reaktionsgleichung

Reaktionsgleichung von HRID 266689
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 10799103(R)-2-(methoxycarbonylamino)-3-phenylpropanoic acidAusbeute 113,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 additonal 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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a6878d43454e41b7a3e35c8089c1bddc
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652245

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