(2S)-2-(phenoxymethyl)oxirane → (S)-N-(2-[2-hydroxy-3-phenoxypropyl]aminoethyl)isobutyramide

HRID 34891Notes

Reaction equation

HRID 34891 reaction equation
[O:1]1[C@H:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[NH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18]>C(O)C>[OH:1][C@H:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 12681828N-(2-Aminoethyl)-2-methylpropanamide

Product 1

HCID 10493020(S)-N-(2-[2-hydroxy-3-phenoxypropyl]aminoethyl)isobutyramideYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-1,2-epoxy-3-phenoxypropane (0.495 g.) and N-(2-aminoethyl)isobutyramide (0.429 g) in ethanol (25 ml) was heated under reflux for 48 hours. The reaction mixture was cooled and solvent removed by rotary evaporation in vacuo. The residual solid was purified by column chromatography on silica (Merck, Art. 7736) using 5% v/v methanol in dichloromethane as eluant. The solid thereby obtained was purified by recrystallisation from ethyl acetate to give (S)-N-(2-[2-hydroxy-3-phenoxypropyl]aminoethyl)isobutyramide (0.425 g), m.p. 88°-89° C., 24 [α]D -5.8° [c, 1.04; methanol], mixed m.p. with material from Example 1, 88°-89° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. temperatureThe reaction mixture was cooled
  4. customsolvent removed by rotary evaporation in vacuo
  5. customThe residual solid was purified by column chromatography on silica (Merck, Art. 7736)
  6. customThe solid thereby obtained
  7. customwas purified by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d6361fc02bb54f1c9603ccba5ef42389
Source dataset
uspto-grants-1988_08
Patent number
US04764361

Reaction notes

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