4-Amino-3-hydroxybutanoic acid → HCID 15224821, compound

HRID 1703455Notes

Reaction equation

HRID 1703455 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[NH2:10][CH2:11][CH:12]([OH:17])[CH2:13][C:14]([OH:16])=O.C1OC1C.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C[Si](C)(C)Cl.C(#N)C>[C:24]([O:26][CH2:27][CH2:28][N:10]1[CH2:11][CH:12]([OH:17])[CH2:13][C:14]1=[O:16])(=[O:25])[CH3:23]

Participants

7

Reactant 4

HCID 21494-Amino-3-hydroxybutanoic acidHCID 6378Propylene OxideHCID 7748Ethyl bromoacetateHCID 13838Hexamethyldisilazane

Product 1

HCID 15224821HCID 15224821, compound

Reagents, catalysts & solvents 2

HCID 6397ChlorotrimethylsilaneCatalystHCID 6342AcetonitrileSolvent

Procedure

Twenty-eight ml. of hexamethyldisilazane and 3 drops of trimethylchlorosilane are added to 10 g. γ-amino-3-hydroxybutyric acid in 100 ml. anhydrous acetonitrile. The reaction mixture is heated under reflux in a current of nitrogen until a clear solution is obtained. The resulting mixture is cooled to ambient temperature and 50 ml. propylene oxide are added thereto, followed by the dropwise addition of 9.4 ml. ethyl bromoacetate. The reaction mixture is heated under reflux for 15 hours, cooled to ambient temperature and then evaporated to dryness in vacuo. The residue obtained, which contains crude 2-(4-trimethyl-silyloxypyrrolidin-2-on-1-yl)-ethyl acetate is separated by chromatography on a eluting silica gel column, using ethyl acetate as elution agent. Eight g. 2-(4-Hydroxypyrrolidin-2-on-1-yl)-ethyl acetate are obtained in the form of a colorless oil; b.p. 180° C./0.8 mm.Hg.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux in a current of nitrogen until a clear solution
  3. customis obtained
  4. additionfollowed by the dropwise addition of 9.4 ml
  5. temperatureThe reaction mixture is heated
  6. temperatureunder reflux for 15 hours
  7. temperaturecooled to ambient temperature
  8. customevaporated to dryness in vacuo
  9. customThe residue obtained
  10. customis separated by chromatography on a eluting silica gel column
  11. washas elution agent

Sources & evidence

ORD record
ord-b8ab3d320ef74801b6c1f70e3031e970
Source dataset
uspto-grants-1978_11
Patent number
US04124594

Reaction notes

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