Hydrochloric Acid → (S)-3-Amino-2-oxo-1-piperidineacetic acid, Ethyl ester

HRID 1941445Notes

Reaction equation

HRID 1941445 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]([OH:18])=[O:17])[C:10]1=[O:19])=O)(C)(C)C.Cl.[CH2:21](O)[CH3:22]>>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]([O:18][CH2:21][CH3:22])=[O:17])[C:10]1=[O:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10778571(S)-2-(3-(tert-Butoxycarbonylamino)-2-oxopiperidin-1-yl)acetic acid

Product 1

HCID 13556450(S)-3-Amino-2-oxo-1-piperidineacetic acid, Ethyl ester

Procedure

To a solution of compound 21 (5.45 g, 0.020 mol) in 20 mL of dry ethanol at 0° was added ethanolic 12N HCl (50.0 mL, 0.60 mol). The solution was stirred at 0° for one hr and then allowed to stir at ambient temperature for 3 hrs. The solvent was evaporated, the residue was twice redissolved in a mixture of ethanol, acetonitrile: 1,1 and reevaporated. After vacuum pumping at <1 mm Hg for 24 hrs, 4.84 g (~quantitative crude yield) of product 22 was obtained as a sticky light brown foam. TLC (silica; CH2Cl2, methanol, conc NH4OH: 27, 3, 1): Rf=0.35.

Workup

  1. stirringto stir at ambient temperature for 3 hrs
  2. customThe solvent was evaporated
  3. dissolutionthe residue was twice redissolved in a mixture of ethanol, acetonitrile
  4. custom1,1 and reevaporated
  5. waitAfter vacuum pumping at <1 mm Hg for 24 hrs

Sources & evidence

ORD record
ord-623af7f184564d05b3db0a8d5881edef
Source dataset
uspto-grants-1997_12
Patent number
US05703208

Reaction notes

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