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Methyl iodide → HCID 86665015, compound

HRID 244379
Notes
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Reaction equation

HRID 244379 reaction equation
[CH2:1]([N:8]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([C:22]([N:24]([CH:38]([CH3:40])[CH3:39])[C@@H:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]3)=[O:23])[C:19]([CH3:21])=[CH:20][C:15]=2[O:14][C:13]([CH2:42][OH:43])([CH3:41])[C:12]1=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:54]I.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[CH2:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([C:22]([N:24]([CH:38]([CH3:39])[CH3:40])[C@@H:25]3[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:26]3)=[O:23])[C:19]([CH3:21])=[CH:20][C:15]=2[O:14][C:13]([CH2:42][O:43][CH3:54])([CH3:41])[C:12]1=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86665014HCID 86665014, compound

Product 1

HCID 86665015HCID 86665015, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the obtained 2-methyl-2-propanyl (3R)-3-[({4-[2-(dibenzylamino)ethyl]-2-(hydroxymethyl)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}carbonyl)(2-propanyl)amino]-1-piperidine carboxylate (22.5 g) in N,N-dimethylformamide (80 ml) were added sodium hydride (1.6 g) and methyl iodide (5.5 g) under ice-cooling. The mixture was stirred for 30 minutes, and then, cooled to room temperature, and further stirred for 2 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, followed by purification with silica gel chromatography to give the title compound (19.2 g).

Workup

  1. temperaturecooling
  2. stirringfurther stirred for 2 hours
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe sodium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customfollowed by purification with silica gel chromatography

Sources & evidence

ORD record
ord-db9a4a0f103c4631bfe03b98b5bf4659
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658639B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes