Hydrochloric Acid → HCID 67641967, compound

HRID 1597763Notes

Reaction equation

HRID 1597763 reaction equation
CON(C)[C:4](=[O:26])[CH:5]([OH:25])[CH:6]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl>O1CCCC1>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][C:4](=[O:26])[CH:5]([OH:25])[CH:6]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86752361HCID 86752361, compoundHCID 178506878HCID 178506878, compound

Product 1

HCID 67641967HCID 67641967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2-hydroxy-4-phenyl-3-[((phenylmethoxy)carbonyl)amino]butanoic acid, N-methoxy-N-methylamide (372 mg, 1.0 mmol) in tetrahydrofuran is cooled to -78° C. and ethyl lithioacetate (72 mg, 3.0 mmol) is added. The solution is stirred at -78° C. for 1 hour, allowed to warm to room temperature, stirred for 1 hour and poured into dilute HCl. The product is extracted by ethyl acetate (3×150 ml) and the combined organic extracts are washed with NaHCO3, dried over Na2SO4 and the solvent removed in vacuo. The crude product is purified by flash chromatography on silica gel.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 hour
  3. extractionThe product is extracted by ethyl acetate (3×150 ml)
  4. washthe combined organic extracts are washed with NaHCO3
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed in vacuo
  7. customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1e62fe412d9f4877bd3513f98cfc083c
Source dataset
uspto-grants-1998_04
Patent number
US05736520

Reaction notes

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