Triethylamine → Dimethylcarbamoylmethyl 1'-{(r)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4'-bipiperidinyl-4-carboxylate

HRID 730681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730681
O[CH2:2][C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[CH2:8]([O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C@@H:24]([O:42][C:43]([N:45]2[CH2:50][CH2:49][CH:48]([N:51]3[CH2:57][CH2:56][C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[NH:53][C:52]3=[O:62])[CH2:47][CH2:46]2)=[O:44])[C:25]([N:27]2[CH2:32][CH2:31][CH:30]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]3)[CH2:29][CH2:28]2)=[O:26])=[CH:18][C:17]=1[CH3:63])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:8]([O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH2:23][C@@H:24]([O:42][C:43]([N:45]2[CH2:46][CH2:47][CH:48]([N:51]3[CH2:57][CH2:56][C:55]4[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=4[NH:53][C:52]3=[O:62])[CH2:49][CH2:50]2)=[O:44])[C:25]([N:27]2[CH2:32][CH2:31][CH:30]([N:33]3[CH2:34][CH2:35][CH:36]([C:39]([O:41][CH2:2][C:3](=[O:4])[N:5]([CH3:7])[CH3:6])=[O:40])[CH2:37][CH2:38]3)[CH2:29][CH2:28]2)=[O:26])=[CH:18][C:17]=1[CH3:63])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 672736911'-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4'-bipiperidinyl-4-carboxylic acid

Produkt 1

HCID 67273082Dimethylcarbamoylmethyl 1'-{(r)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]propionyl}-1,4'-bipiperidinyl-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

30 mg (0.29 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added at RT to a solution of 200 mg (0.25 mmol) 1′-{(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyloxy]-propionyl}-1,4′-bipiperidinyl-4-carboxylic acid (Example 6.1a), 90 mg (0.28 mmol) TBTU and 80 μL (3.73 mmol) triethylamine in 1.8 mL DMF and this was stirred for 20 h at RT. The reaction mixture was poured onto saturated NaHCO3 solution, the precipitate formed was suction filtered and dried. Further purification was carried out by HPLC, the fractions containing the product were combined and lyophilised.

Aufarbeitung

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customdried
  4. customFurther purification
  5. additionthe fractions containing the product

Quellen und Nachweise

ORD-Eintrag
ord-645f55898c594f5aa4a73c9373f636fb
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582625B2

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