Water → HCID 67385665, compound

HRID 1410285Notes

Reaction equation

HRID 1410285 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].[C:22]1([CH2:28][CH2:29][CH:30]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(#N)C.C(OCC)(=O)C>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][S:8][C:7]1[CH:6]=[CH:5][C:4](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])=[CH:3][C:2]=1[NH:1][CH2:30][CH2:29][CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 7707BenzenepropanalHCID 5049666Sodium triacetoxyborohydrideHCID 67385624HCID 67385624, compound

Product 1

HCID 67385665HCID 67385665, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

250 mg (0.62 mmol) of (E)-methyl 3-(3-amino-4-(2-(diethylamino)ethylthio)-phenyl)acrylate was suspended in acetonitrile (5 mL) and to this solution, 3-phenylpropionaldehyde (108 mg, 0.8 mmol) was added under stirring. Then, sodium triacetoxyborohydride (636 mg, 3 mmol) was added and the resulted mixture was stirred at room temperature for 3-60 hours. Water and ethyl acetate was added after removing the solvent—acetonitrile. Collecting organic layers and drying it, 229 mg of (E)-methyl 3-(4-(2-(diethylamino)ethylthio)-3-(3-phenylpropylamino)phenyl)acrylate was obtained in a form of an oily product after being purified by chromatography. Yield: 86.6%. TLC: Rf=0.6 (DCM:MeOH=9:1). HPLC: 91%; tR=9.90 min (LC/PDA: Diamonsil C18.5μ 150×4.6 mm, flow rate 1.0 mL/min, grade: 10-100% B, 18 minutes; mobile phase A: H2O; mobile phase B: acetonitrile; UV254). MS (m/z): 427 (MH)+.

Workup

  1. additionwas added
  2. stirringthe resulted mixture was stirred at room temperature for 3-60 hours
  3. customafter removing the solvent—acetonitrile
  4. customCollecting organic layers and drying it

Sources & evidence

ORD record
ord-8d6e6d865ad84c7c95c705b2eb5d36ff
Source dataset
uspto-grants-2014_12
Patent number
US08921424B2

Reaction notes

Loading…