Ammonium Hydroxide → HCID 60206919, compound

HRID 1991548Notes

Reaction equation

HRID 1991548 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:5][C@H:6]([NH:24][C:25](=[O:27])[CH3:26])[C@H:7]([OH:23])[CH2:8][NH:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH3:21])[CH:18]=2)[N:13]([CH3:22])[CH2:12][CH2:11]1.[OH-].[NH4+]>CO.ClCCl>[F:31][C:29]1[CH:28]=[C:4]([CH:3]=[C:2]([F:1])[CH:30]=1)[CH2:5][C@H:6]([NH:24][C:25](=[O:27])[CH3:26])[C@H:7]([OH:23])[CH2:8][NH:9][C@@H:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH3:21])[CH:18]=2)[N:13]([CH3:22])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10320544HCID 10320544, compound

Product 1

HCID 60206919HCID 60206919, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Silica gel chromatography of approximately 0.1 g of N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(6-ethyl-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino]-2-hydroxypropyl}acetamide using methanol/dichloromethane (8/92) with 0.1% ammonium hydroxide gave 0.032 g of N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[(4S)-6-ethyl-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-hydroxypropyl)acetamide [Rf (MeOH/CH2Cl2/NH4OH)=0.40; MS (ESI+) for C24H31F2N3O2 m/z 432.2 (M+H)+]. Re-chromatography of mixed fractions gave 0.011 g of a 9:1 mixture of the 4R isomer [Rf (MeOH/CH2Cl2/NH4OH)=0.35; MS (ESI+) for C24H31F2N3O2 m/z 432.2 (M+H)+] and the 4S isomer.

Sources & evidence

ORD record
ord-29161484ff1a4328ad6c732c844d67c0
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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