Hydrochloric Acid → HCID 18606088, compound

HRID 979836Notes

Reaction equation

HRID 979836 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]([OH:14])=[O:13])=[O:5])[CH3:3].Cl.[OH-].[Na+].O=[C:19]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([BH3-])#N.[Na+]>C(O)C>[C:20]([C@@H:19]([NH:1][C@H:2]([C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:11][C:12]([OH:14])=[O:13])=[O:5])[CH3:3])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 18606086HCID 18606086, compound

Product 1

HCID 18606088HCID 18606088, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of L-alanyl-(S)-2-pyrrolidineacetic acid (390 mg; 2.0 mmol) (from the hydrochloride neutralized with 2.5N NaOH) and ethyl 2-oxo-4-phenylbutyrate (1.00 g) in 5 ml of ethanol is added 1 g of ground 4A molecular sieves. The mixture is stirred for 30 minutes and sodium cyanoborohydride (310 mg) is added in portions over 2 hours. The mixture is stirred overnight, filtered, and the filtrate concentrated under reduced pressure to near dryness. The mixture is taken up in methylene chloride and washed with water. The methylene chloride layer is extracted with 5% aqueous potassium bicarbonate, the latter extract is acidified to pH 2 and extracted with methylene chloride. The organic extract is dried over sodium sulfate and concentrated to dryness under reduced pressure to give the desired product. The S,S,S and R,S,S diastereomers are separated using reverse phase HPLC.

Workup

  1. stirringThe mixture is stirred overnight
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washwashed with water
  5. extractionThe methylene chloride layer is extracted with 5% aqueous potassium bicarbonate
  6. extractionthe latter extract
  7. extractionextracted with methylene chloride
  8. extractionThe organic extract
  9. dry with materialis dried over sodium sulfate
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-57c4f43f45cf4863aaa7d05a8bb54126
Source dataset
uspto-grants-1987_01
Patent number
US04634716

Reaction notes

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