Propanal → Methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}amino)phenyl]propanoate

HRID 508042Notes

Reaction equation

HRID 508042 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30](/[N:33]=[CH:34]/[C:35]2[S:36][CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:39]=2)=[CH:29][CH:28]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:60](=O)[CH2:61][CH3:62].C(=O)([O-])O.[Na+]>ClCCCl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]([CH2:34][C:35]2[S:36][CH:37]=[C:38]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:39]=2)[CH2:60][CH2:61][CH3:62])=[CH:29][CH:28]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 527PropanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178499916HCID 178499916, compound

Product 1

HCID 23157528Methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}amino)phenyl]propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The yellow oil obtained in Example 50 was dissolved in 1,2-dichloroethane (20 mL), sodium triacetoxyborohydride (1.26 g, 6.0 mmol) was added at room temperature by small portions, and the mixture was stirred at room temperature for 60 hr. Propionaldehyde (200 mg, 3.0 mmol) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane) to give the title compound (549 mg, yield 80%, 2 steps) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-05fb64052947452f94348111f83567b1
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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