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Methyl iodide → HCID 86750226, compound

HRID 234717
Notes
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Reaction equation

HRID 234717 reaction equation
[H-].[Na+].[C:3]1([N:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:10](=[O:30])[NH:11][NH:12][CH2:13][CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:15]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CI.[CH3:39]N(C)P(N(C)C)(N(C)C)=O>O1CCCC1.C(OCC)(=O)C.O>[CH3:39][N:12]([CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:15]1)[NH:11][C:10]([N:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 86750225HCID 86750225, compound

Product 1

HCID 86750226HCID 86750226, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent2×
HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (6.1 mg) in tetrahydrofuran (1.5 ml) was added a solution of the compound prepared in example 15 (70 mg) in tetrahydrofuran (3 ml) under an atmosphere of argon. The mixture was stirred for 30 min at room temperature. To the mixture were successively added methyl iodide (261 mg) and hexamethylphosphoramide (1 ml), After stirred for 2 h at room temperature, the mixture was diluted with ethyl acetate and water. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane =2:3) to give the title compound (27 mg) having the following physical data.

Workup

  1. stirringAfter stirred for 2 h at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane =2:3)

Sources & evidence

ORD record
ord-0a40a64eb5fd4534b8890b7eadef87df
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05596009

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes