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

HRID 2108056Notes

Reaction equation

HRID 2108056 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)isobutyramide

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), m.p. 88°-89° C., 24 [α]D -5.8° [c, 1.04; methanol], mixed m.p. with material from Preparation 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-915a5e468f4a4f0dae600c46f9a8c7db
Source dataset
uspto-grants-1990_06
Patent number
US04937267

Reaction notes

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