N-(4-((oxiran-2-yl)methoxy)phenyl)acetamide → (RS)-6-chloro-alpha-[[[(R)-p-(2-ethoxyethoxy)-alpha-methylphenethyl]amino]methyl]-2-pyridinemethanol

HRID 2292068Notes

Reaction equation

HRID 2292068 reaction equation
O1CC1COC1C=CC(NC(=O)C)=CC=1.[Cl:16][C:17]1[N:22]=[C:21]([CH:23]([OH:56])[CH2:24][N:25]([C@H:41]([CH3:55])[CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH2:51][O:52][CH2:53][CH3:54])=[CH:45][CH:44]=2)CC(O)COC2C=CC(NC(=O)C)=CC=2)[CH:20]=[CH:19][CH:18]=1>CO>[Cl:16][C:17]1[N:22]=[C:21]([CH:23]([CH2:24][NH:25][C@H:41]([CH3:55])[CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:49][CH2:50][CH2:51][O:52][CH2:53][CH3:54])=[CH:47][CH:48]=2)[OH:56])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2798712N-(4-((oxiran-2-yl)methoxy)phenyl)acetamideHCID 53790281HCID 53790281, compound

Product 1

HCID 54562232(RS)-6-chloro-alpha-[[[(R)-p-(2-ethoxyethoxy)-alpha-methylphenethyl]amino]methyl]-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

using 4'-(2,3-epoxypropoxy)acetanilide there were obtained from 1.0 g of (RS)-6-chloro-α-[[[(R)-p-(2-ethoxyethoxy)-α -methylphenethyl]amino]methyl]-2-pyridinemethanol (Example 4C) 530 mg of 4'-[(RS)-3-[[(RS)-2-(6-chloro-2-pyridyl)-2-hydroxyethyl][(R)-p-(2-ethoxyethoxy)-α-methylphenethyl]amino]-2-hydroxypropoxy]acetanilide, [α]D20° =-39° (c=0.4 in MeOH),

Sources & evidence

ORD record
ord-3a02fec44b0e42619f2aaa90717bfd28
Source dataset
uspto-grants-1989_01
Patent number
US04800206

Reaction notes

Loading…