Acetic Acid → HCID 17958610, compound

HRID 2243302Notes

Reaction equation

HRID 2243302 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([OH:11])(=[O:10])C.[CH:12]([CH:14]([CH2:24][CH:25]1[CH:30]=[CH:29][C:28](OC)=[CH:27][C:26]1=C=O)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22]C)=[O:20])=O.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[NH:1]([CH2:12][CH:14]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:8]([O:11][CH3:35])=[O:10])=[CH:29][CH:30]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 86618864HCID 86618864, compound

Product 1

HCID 17958610HCID 17958610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

30.0 mg (0.33 mmol) of aniline are dissolved in dichloromethane and 0.02 ml of acetic acid and a solution of 90.6 mg (0.30 mmol) of ethyl 6-forrnyl-7-(4-methoxy-carbonylphenyl)heptanoate (synthesis cf. EP-A-0 341 551, p. 32, Ex. 44) in dichloromethane are added. After 30 minutes at room temperature, the solution is cooled to 0° C., and 87.7 mg (0.41 mmol) of sodium triacetoxyborohydride are added. The reaction mixture is stirred at room temperature for 18 hours, 0.2 ml of water are added and the mixture is filtered through Extrelut. For purification, the substance is chromatographed on 10 g of silica gel 60 (particle size 0.040-0.063 mm) using the mobile phase cyclohexane/ethyl acetate 3:1 to 1:1.

Workup

  1. filtrationthe mixture is filtered through Extrelut
  2. customFor purification
  3. customthe substance is chromatographed on 10 g of silica gel 60 (particle size 0.040-0.063 mm)

Sources & evidence

ORD record
ord-b1806bf13f314c0c8fa9196d9bc0f9ae
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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