Methyl iodide → HCID 21996653, compound

HRID 1978293Notes

Reaction equation

HRID 1978293 reaction equation
[H-].[Na+].[C:3]1([CH3:50])[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[S:11]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([S:38]([C:41]1[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=1[CH3:49])(=[O:40])=[O:39])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][S:26]([C:29]1[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=1[CH3:37])(=[O:28])=[O:27])(=[O:13])=[O:12].IC.[CH3:53][CH2:54]CCCC.[CH3:59]COC(C)=O>CN(C=O)C>[C:5]1([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH3:50])[C:4]=1[S:11]([N:14]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([S:38]([C:41]1[C:42]([CH3:49])=[CH:43][C:44]([CH3:48])=[CH:45][C:46]=1[CH3:47])(=[O:39])=[O:40])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([S:26]([C:29]1[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=1[CH3:37])(=[O:27])=[O:28])[CH2:53][CH3:54])[CH3:59])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10604917HCID 10604917, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 21996653HCID 21996653, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 0.28 g, 6.9 mmol), 33 (2.16 g, 3.0 mmol), and iodomethane (6.1 mL, 9.8 mmol) in DMF (30 mL) were combined and worked up by the method of 43. Column chromatography (7:3 hexane/EtOAc) gave 1.90 g (85%) of 53 as an oil: NMR δ 1.08-1.16 (m, 2 H), 1.38-1.50 (m, 8 H ), 2.28-2.29 (2 s, 9 H), 2.57-2.58 (2 s, 18 H), 2.63 (s, 3 H), 2.65 (s, 3 H), 3.02-3.14 (m, 8 H), 6.95 (s, 6 H); HRMS calcd. for C38H58N3O6S3 748.3487 (M+H), found. 748.3483 (M+H).

Sources & evidence

ORD record
ord-7aff1cbb34344306978ec97deea462f6
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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