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Dimethylformamide → HCID 59571721, compound

HRID 2194308
Notes
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Reaction equation

HRID 2194308 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]1[O:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][C:10]=1[CH2:20][O:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[C:35]([OH:40])[C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:24][C:23]=1[O:43][CH3:44].Br[C@H:46]([CH2:52][CH3:53])[C:47]([O:49][CH2:50][CH3:51])=[O:48]>O>[CH3:44][O:43][C:23]1[CH:24]=[C:25]([CH:41]=[CH:42][C:22]=1[O:21][CH2:20][C:10]1[N:11]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:13][C:9]=1[CH3:8])[CH2:26][N:27]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([O:40][C@@H:46]([CH2:52][CH3:53])[C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:34]=2[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7000062130251-07-9HCID 59571732HCID 59571732, compound

Product 1

HCID 59571721HCID 59571721, compound

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

41 mg of sodium hydride (60%) was added to N,N-dimethylformamide (2.5 mL) solution of 500 mg of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-9H-carbazole-4-ol while being cooled in an ice bath, and stirred at room temperature for 1 hour. Thereafter, 239 mg of ethyl (R)-2-bromobutyrate was added thereto dropwise at −5° C., and was stirred for 30 minutes. Water was added to the reaction mixture, and extracted twice with ethyl acetate. The combined extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:4), and 650 mg of the subject compound was prepared. Optical purity 95% ee (HPLC).

Workup

  1. temperaturewhile being cooled in an ice bath
  2. stirringdropwise at −5° C., and was stirred for 30 minutes
  3. extractionextracted twice with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:4), and 650 mg of the subject compound
  10. customwas prepared

Sources & evidence

ORD record
ord-cd99b0be457249f3b45574a6b0d4a77a
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329913B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes