(R)-N-(2-(Benzyloxy)-5-(oxiran-2-yl)phenyl)formamide → 5-{(1R)-2-[Benzyl(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(benzyloxy)phenylformamide

HRID 2118358Notes

Reaction equation

HRID 2118358 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:34]1[CH2:36][C@H:35]1[C:37]1[CH:38]=[CH:39][C:40]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[C:41]([NH:43][CH:44]=[O:45])[CH:42]=1>C1COCC1>[CH2:1]([N:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:27])=[O:28])[CH:21]=1)[CH2:36][C@@H:35]([C:37]1[CH:38]=[CH:39][C:40]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[C:41]([NH:43][CH:44]=[O:45])[CH:42]=1)[OH:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11489356(R)-N-(2-(Benzyloxy)-5-(oxiran-2-yl)phenyl)formamideHCID 69119361N-Benzyl-6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexan-1-amine

Product 1

HCID 866076805-{(1R)-2-[Benzyl(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(benzyloxy)phenylformamideYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyl-6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexan-1-amine (40 mg) was dissolved in dry THF (0.25 ml) and {5-[(2R)-2-oxiranyl]-2-[(phenylmethyl)oxy]phenyl}formamide (23 mg) (Organic Process Research & Development 1998, 2, 96-99), added. The reaction mixture was heated in a microwave oven for 3 h at 150°. The solvent was removed and the residue purified on a silica SPE bond elut cartridge, eluting with EtOAc-cyclohexane mixtures to give the title compound, (17 mg) LCMS RT=3.1 min

Workup

  1. temperatureThe reaction mixture was heated in a microwave oven for 3 h at 150°
  2. customThe solvent was removed
  3. customthe residue purified on a silica SPE bond elut cartridge
  4. washeluting with EtOAc-cyclohexane mixtures

Sources & evidence

ORD record
ord-330c033169404609885443fb8056d259
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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