Acetaldehyde → methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate

HRID 1786048Notes

Reaction equation

HRID 1786048 reaction equation
C([N:4]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][CH:24]([NH:29][C:30](OC(C)(C)C)=O)[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:39])[CH2:6]1)(=O)C.Cl.[C:48](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:49].[Na+].[CH:62](=[O:64])[CH3:63].Cl[CH2:66]Cl>O1CCOCC1>[C:62]([N:4]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:30][CH3:66])[CH2:48][CH3:49])[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:39])[CH2:6]1)(=[O:64])[CH3:63]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 68919251methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate

Product 1

HCID 68920582methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoateYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-[(tert-butoxycarbonyl)amino]butanoate was dissolved in 20 ml dichloromethane and 4 ml HCl in dioxane (4M) was added. The mixture was stirred 2 hours and concentrated down. The residue was washed with ether, then partition between 1M NaOH and dichloromethane. The dichloromethane layer was removed and dried with MgSO4. Sodium triacetoxyborohydride (0.61 g, 2.9 mmol) and acetaldehyde (0.33 ml, 5.8 mmol) was added. The mixture was stirred 2 days and washed with 1M NaOH. The mixture was then concentrated and purified by silica gel chromatography (40% CH2Cl2/60% EtOAc) to afford methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate (0.075 g, 17%).

Workup

  1. concentrationconcentrated down
  2. washThe residue was washed with ether
  3. custompartition between 1M NaOH and dichloromethane
  4. customThe dichloromethane layer was removed
  5. dry with materialdried with MgSO4
  6. stirringThe mixture was stirred 2 days
  7. washwashed with 1M NaOH
  8. concentrationThe mixture was then concentrated
  9. custompurified by silica gel chromatography (40% CH2Cl2/60% EtOAc)

Sources & evidence

ORD record
ord-d95e765282f44d56bf005c74a09506bf
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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