Sodium Bicarbonate → HCID 22851701, compound

HRID 55463Notes

Reaction equation

HRID 55463 reaction equation
Cl.[NH2:2][C@H:3]1[C@H:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@@H:7]([CH3:14])[O:6][C:4]1=[O:5].C(=O)(O)[O-:16].[Na+]>C(Cl)Cl>[NH2:2][C@@H:3]([C@H:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@H:7]([OH:6])[CH3:14])[C:4]([OH:16])=[O:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22851702HCID 22851702, compound

Product 1

HCID 22851701HCID 22851701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

56.0 g of 2(S)-amino-3(S)-ethoxycarbonyl-4(R)-pentanolide hydrochloride are dissolved in methylene chloride and the pH is adjusted to 7.5 with sodium bicarbonate solution. The methylene chloride phase is separated off, the aqueous phase is saturated with sodium chloride and extracted repeatedly with methylene chloride, and the organic phases are concentrated by evaporation. 106 ml of 2N sodium hydroxide solution are added dropwise to the residue in 120 ml of ethanol at 0° C. within a period of 6 hours. The solution is then concentrated to half its volume, adjusted to pH 3.9 with 103 ml of 2N hydrochloric acid, and completely concentrated by evaporation. The residue is crystallised from isopropanol/diisopropyl ether, stirred up with methanol and filtered over silica gel. [α]36520 =+14.5° (1% in H2O), m.p. 150°-151° C.

Workup

  1. customThe methylene chloride phase is separated off
  2. extractionextracted repeatedly with methylene chloride
  3. concentrationthe organic phases are concentrated by evaporation
  4. addition106 ml of 2N sodium hydroxide solution are added dropwise to the residue in 120 ml of ethanol at 0° C. within a period of 6 hours
  5. concentrationThe solution is then concentrated to half its volume
  6. concentrationcompletely concentrated by evaporation
  7. customThe residue is crystallised from isopropanol/diisopropyl ether
  8. filtrationfiltered over silica gel
  9. custom[α]36520 =+14.5° (1% in H2O), m.p. 150°-151° C.

Sources & evidence

ORD record
ord-78056d09af0c465b912e219ae1dcf02e
Source dataset
uspto-grants-1997_04
Patent number
US05625059

Reaction notes

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