(2S)-2-(phenoxymethyl)oxirane → (2S)-3-(4-nitrophenyl)-2-[((2S)-2-hydroxy-3-phenoxypropyl)amino]-1-propanol

HRID 2417406Notes

Reaction equation

HRID 2417406 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@H:13]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH2:14][OH:15]>C(O)C>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@H:13]([NH:12][CH2:11][C@H:9]([OH:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14][OH:15])=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 10397777(S)-2-Amino-3-(4-nitrophenyl)propan-1-ol

Product 1

HCID 69817987(2S)-3-(4-nitrophenyl)-2-[((2S)-2-hydroxy-3-phenoxypropyl)amino]-1-propanolYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2S)-2-(phenoxymethyl)oxirane (2.30 g), (2S)-2-amino-3-(4-nitrophenyl)-1-propanol (3.0 g) and ethanol (30 ml) was heated under reflux for 18 hours. The reaction mixture was evaporated in vacuo. The residue was triturated with ethyl acetate to give (2S)-3-(4-nitrophenyl)-2-[((2S)-2-hydroxy-3-phenoxypropyl)amino]-1-propanol (3.97 g) as a pale yellow powder. This powder was used for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-455e363fce664de4bdb8f457981de08b
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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