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Formic Acid → (R)-1-(4-formyloxy-3,5-dimethyl-benzyl)-2-oxo-2-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 491122
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Reaktionsgleichung von HRID 491122
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[O:11]=[C:12]1[N:18]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C@H:28]([CH2:43][C:44]3[CH:49]=[C:48]([CH3:50])[C:47]([OH:51])=[C:46]([CH3:52])[CH:45]=3)[C:29](=[O:42])[N:30]3[CH2:35][CH2:34][N:33]([CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH2:32][CH2:31]3)=[O:26])[CH2:21][CH2:20]2)[CH2:17][CH2:16][C:15]2[CH:53]=[CH:54][CH:55]=[CH:56][C:14]=2[NH:13]1>C(Cl)Cl>[O:11]=[C:12]1[N:18]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C@H:28]([CH2:43][C:44]3[CH:49]=[C:48]([CH3:50])[C:47]([O:51][CH:1]=[O:3])=[C:46]([CH3:52])[CH:45]=3)[C:29](=[O:42])[N:30]3[CH2:31][CH2:32][N:33]([CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH2:34][CH2:35]3)=[O:26])[CH2:21][CH2:20]2)[CH2:17][CH2:16][C:15]2[CH:53]=[CH:54][CH:55]=[CH:56][C:14]=2[NH:13]1
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Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11857998(R)-1-(4-hydroxy-3,5-dimethyl-benzyl)-2-oxo-2-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Produkt 1

HCID 11857474(R)-1-(4-formyloxy-3,5-dimethyl-benzyl)-2-oxo-2-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 25 μL acetic anhydride and 0.5 mL formic acid in 1 mL DCM was stirred for 2 h at RT (formation of the mixed anhydride). Then 38 mg (0.06 mmol) (R)-1-(4-hydroxy-3,5-dimethyl-benzyl)-2-oxo-2-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate was added (Example 7i) and the reaction mixture was stirred overnight at RT. The reaction solution was evaporated down and the residue was again added to a solution of the mixed anhydride and stirred overnight at RT. The mixture was evaporated down i.vac. and the residue was purified by HPLC. The fractions containing the product were combined and lyophilised.

Aufarbeitung

  1. customThe reaction solution was evaporated down
  2. additionthe residue was again added to a solution of the mixed anhydride
  3. stirringstirred overnight at RT
  4. customThe mixture was evaporated down i.vac
  5. customand the residue was purified by HPLC
  6. additionThe fractions containing the product

Quellen und Nachweise

ORD-Eintrag
ord-b01e064f9a8c4d38947ed81a484036fa
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07528129B2

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