Hydrochloric Acid → HCID 15578596, compound

HRID 729015Notes

Reaction equation

HRID 729015 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[O:15][CH2:16][CH:17]1[O:19][CH2:18]1.[OH-].[Na+]>>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[O:15][CH2:16][CH:17]([OH:19])[CH2:18][NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 419889Ethyl 3-aminopropanoateHCID 129593782-[(3-methoxyphenoxy)methyl]oxirane

Product 1

HCID 15578596HCID 15578596, compound

Procedure

This compound was prepared in accordance with Example 1 using 7.6 g of the hydrochloride of ethyl 3-aminopropanoate, 4.5 g of 3-(3-methoxyphenoxy)-1,2-epoxypropane, and 2.0 g of NaOH. The crude product was washed with 150 ml of water and dissolved in 100 ml of water and 10 ml of 2-n HCl. This solution was extracted with ethyl acetate, treated with NaHCO3, and extracted with CH2Cl2. The organic layer was separated, dried over MgSO4, filtered and evaporated. Ethyl N-[3-(2-cyano-4-methoxyphenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized. Yield 1.2 g. Melting point 72° C. (base). The structure was determined by NMR.

Workup

  1. washThe crude product was washed with 150 ml of water
  2. dissolutiondissolved in 100 ml of water
  3. extractionThis solution was extracted with ethyl acetate
  4. additiontreated with NaHCO3
  5. extractionextracted with CH2Cl2
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customEthyl N-[3-(2-cyano-4-methoxyphenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized

Sources & evidence

ORD record
ord-4187494a97114343b795371f21d4d307
Source dataset
uspto-grants-1991_09
Patent number
US05051446

Reaction notes

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