Triethylamine → 2-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl ester

HRID 858366Notes

Reaction equation

HRID 858366 reaction equation
C(Cl)(=O)C(C)(C)C.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH2:22][C:23]([OH:25])=O)[CH:14]=[CH:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:9].C(N(CC)CC)C.[CH3:33][CH:34]([CH3:50])[CH2:35][C@H:36]([NH2:49])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>C1(C)C=CC=CC=1.CCCCCC>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH2:22][C:23]([NH:49][C@H:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N:43]2[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]2)[CH2:35][CH:34]([CH3:50])[CH3:33])=[O:25])[CH:14]=[CH:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 101312123-Ethoxy-4-ethoxycarbonylphenylacetic acidHCID 105146093-Methyl-1-(2-piperidinophenyl)-1-butylamine, (S)-

Product 1

HCID 106484192-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

Pivaloyl chloride (5.4 g, 45 mmol) was added to a mixture of 3-ethoxy-4-ethoxycarbonyl phenylacetic acid (10.0 g, 40 mmol), toluene (50 ml) and triethylamine (5.0 g, 49 mmol) at −5° C. and stirred for 1 hour. A solution of (S)-3-methyl-1-(2-piperidinophenyl)-1-butylamine (9.8 g, 40 mmol) in toluene (20 ml) was then added at below 10° C. The temperature of the reaction mixture was raised to 30° C. and the mixture stirred overnight. It was then washed with water and saturated sodium bicarbonate solution. Toluene was distilled off under reduced pressure to get the crude product. The crude product was dissolved in toluene (35 ml), hexane (200 ml) was added and the mixture cooled at 0° C. The solid product so obtained was filtered and dried to give 14.0 g of the title compound (Yield: 73%, HPLC Purity 99%).

Workup

  1. stirringthe mixture stirred overnight
  2. washIt was then washed with water and saturated sodium bicarbonate solution
  3. distillationToluene was distilled off under reduced pressure
  4. customto get the crude product
  5. temperaturethe mixture cooled at 0° C
  6. customThe solid product so obtained
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-f8329fcb31f64a37ba5427f9c5fdadb5
Source dataset
uspto-grants-2006_12
Patent number
US07148355B2

Reaction notes

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