Hydrochloric Acid → HCID 54203704, compound

HRID 729013Notes

Reaction equation

HRID 729013 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[O:10]1[CH2:22][CH:11]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].[OH-].[Na+]>C(OCC)(=O)C>[C:17]([C:16]1[CH:15]=[C:14]([CH:21]=[CH:20][CH:19]=1)[O:13][CH2:12][CH:11]([OH:10])[CH2:22][NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 419889Ethyl 3-aminopropanoateHCID 246884053-[(Oxiran-2-yl)methoxy]benzonitrile

Product 1

HCID 54203704HCID 54203704, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared in accordance with Example 1 using 15.36 g of the hydrochloride of ethyl 3-aminopropanoate, 8.7 g of 3-(2,3-epoxypropoxy)benzonitrile, and 4.0 g of NaOH. The crude oil was dissolved in 200 ml of ethyl acetate, washed twice with water, and extracted with 2-n HCl. The pH of the water phase was adjusted to 9.5 and the solution extracted with ethyl acetate. The ethyl acetate phase was dried with MgSO4, filtered and evaporated. Ethyl N-[3-(3-cyanophenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized. Yield 2 g. Melting point 95° C. (base). The structure was determined using NMR.

Workup

  1. washwashed twice with water
  2. extractionextracted with 2-n HCl
  3. extractionthe solution extracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase was dried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customEthyl N-[3-(3-cyanophenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized

Sources & evidence

ORD record
ord-4b8cb47011754a2e97764678532eb190
Source dataset
uspto-grants-1991_09
Patent number
US05051446

Reaction notes

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