(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane → HCID 69818222, compound

HRID 2417419Notes

Reaction equation

HRID 2417419 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:27][C@@H:28]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)[CH2:29][OH:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[CH2:20]([N:27]([C@@H:28]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=1)[CH2:29][OH:30])[CH2:17][C@H:15]([OH:16])[CH2:14][O:13][C:12]1[CH:18]=[CH:19][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxiraneHCID 69818787HCID 69818787, compound

Product 1

HCID 69818222HCID 69818222, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2S)-2-[(4-(benzyloxy)phenoxy)methyl]-oxirane (1.19 g) and (2S)-2-(benzylamino)-3-(4-nitrophenyl)-1-propanol (1.33 g) in ethanol (13 ml) was refluxed for 20 hours. After cooling to room temperature, the solvent was removed by evaporation and the residue was chromatographed on silica gel (eluent: chloroform/methanol=98/2) to give (2S)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-3-(4-nitrophenyl)-1-propanol (2.04 g) as a yellow gum.

Workup

  1. customthe solvent was removed by evaporation
  2. customthe residue was chromatographed on silica gel (eluent: chloroform/methanol=98/2)

Sources & evidence

ORD record
ord-c4544797cf0145bdb175122a84f12e74
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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