Triethylamine → HCID 66905942, compound

HRID 1691762Notes

Reaction equation

HRID 1691762 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([C@@H:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:22])[CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:41][C:42]1([CH3:50])[CH2:48][C:47](=[O:49])[O:46][C:44](=[O:45])[CH2:43]1.C(=O)([O-])O.[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:7]([CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:47](=[O:49])[CH2:48][C:42]([CH3:50])([CH3:41])[CH2:43][C:44]([OH:46])=[O:45])[CH2:11][CH:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C@@H:21]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:22])=[O:33])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 778133,3-Dimethylglutaric anhydrideHCID 516892Sodium BicarbonateHCID 59178521HCID 59178521, compound

Product 1

HCID 66905942HCID 66905942, compoundYield 111.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 181 mg of tert-butyl[(1R)-1-(1-naphthyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate, 0.114 mL of triethylamine, and 3.0 mL of THF was added 64 mg of 3,3-dimethylglutaric anhydride at room temperature, followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by stirring, extracting with chloroform, and drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 266 mg of 5-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-3,3-dimethyl-5-oxopentanoic acid as a crude product. ESI+: 587

Workup

  1. stirringby stirring
  2. extractionextracting with chloroform
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9db32651bca483b89988c1db3c896df
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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