Dibenzylamine → {5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[(phenylmethyl)oxy]phenyl}formamide

HRID 494166Notes

Reaction equation

HRID 494166 reaction equation
[O:1]1[CH2:3][C@H:2]1[C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([NH:10][CH:11]=[O:12])[CH:9]=1.[CH2:21]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([CH2:21][N:28]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:3][C@@H:2]([C:4]2[CH:5]=[CH:6][C:7]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]([NH:10][CH:11]=[O:12])[CH:9]=2)[OH:1])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 7656DibenzylamineHCID 11489356(R)-N-(2-(Benzyloxy)-5-(oxiran-2-yl)phenyl)formamide

Product 1

HCID 86606166{5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[(phenylmethyl)oxy]phenyl}formamide

Procedure

A mixture of {5-[(2R)-2-oxiranyl]-2-[(phenylmethyl)oxy]phenyl}formamide (WO 0276933) (200 mg) and dibenzylamine (0.75 ml) were heated in a microwave oven at 150° for 30 min. The mixture was allowed to cool to 20° and was purified on a silica SPE bond elut cartridge (10 g) using a gradient of 0% to 50% EtOAc in cyclohexane (Gradmaster™). The appropriate fractions were evaporated in vacuo and the residue further purified by mass-directed autopreparative HPLC to give the title compound (123 mg). LCMS RT=2.75 min.

Workup

  1. temperaturewere heated in a microwave oven at 150° for 30 min
  2. temperatureto cool to 20°
  3. customwas purified on a silica SPE bond elut cartridge (10 g)
  4. customThe appropriate fractions were evaporated in vacuo
  5. customthe residue further purified by mass-directed autopreparative HPLC

Sources & evidence

ORD record
ord-a554398fb4514f4a8337416e4ec43232
Source dataset
uspto-grants-2009_05
Patent number
US07538127B2

Reaction notes

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