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 1786048ノート

反応式

HRID 1786048 の反応式
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]

参加物

7

反応物 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

生成物 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)butanoate収率 17%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d95e765282f44d56bf005c74a09506bf
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

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