Hydrochloric Acid → HCID 69520495, compound

HRID 1828375Notes

Reaction equation

HRID 1828375 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:7][C:8]([NH:10][C@@H:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:12]([OH:16])[C:13]([OH:15])=[O:14])=[O:9])[CH3:6].S(=O)(O)O.Cl.[CH3:29]O>C1(C)C=CC=CC=1>[CH3:29][O:14][C:13](=[O:15])[C@@H:12]([OH:16])[C@@H:11]([NH:10][C:8]([O:7][CH2:5][CH3:6])=[O:9])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 1100Sulfurous AcidHCID 24386Thionyl Chloride2×HCID 11437077HCID 11437077, compound

Product 1

HCID 69520495HCID 69520495, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (596 mg) was added to methanol (1.39 g) over 10 minutes under ice-cooling, and the mixture was reacted at the same temperature for 1 hour. The resultant solution was added to a solution of (2S,3S)-3-(ethoxycarbonyl)amino-2-hydroxy-4-phenylbutyric acid (HPLC area ratio of erythro-isomer/threo-isomer=99/1) (1.04 g) and toluene (10 ml) over 10 minutes under ice-cooling. The mixture was reacted at the same temperature for 2 hours and then warmed to room temperature. From the resultant reaction solution, methanol and thionyl chloride as well as components secondarily produced from these reagents and having a low boiling point such as sulfurous acid, hydrogen chloride or the like were distilled off under reduced pressure. Tetrahydrofuran was added to the resultant residue to obtain a tetrahydrofuran solution (10.12 g) of (2S,3S)-3-(ethoxycarbonyl)amino-2-hydroxy-4-phenylbutyric acid methyl ester. The HPLC area ratio of erythro-isomer/threo-isomer was 99/1, and the diastereomer excess was 99% d.e.

Workup

  1. temperaturecooling
  2. customthe mixture was reacted at the same temperature for 1 hour
  3. temperaturecooling
  4. customThe mixture was reacted at the same temperature for 2 hours
  5. customsecondarily produced from these reagents
  6. distillationthe like were distilled off under reduced pressure
  7. additionTetrahydrofuran was added to the resultant residue

Sources & evidence

ORD record
ord-305c669eae9c4a6a840e488e507063d4
Source dataset
uspto-grants-2006_06
Patent number
US07057066B2

Reaction notes

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