Sodium hydride → HCID 21996667, compound

HRID 1978294Notes

Reaction equation

HRID 1978294 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].I[CH2:52][CH2:53][CH3:54].[CH3:55][CH2:56]CCCC.CCOC(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])[CH2:55][CH3:56])[CH2:52][CH2:53][CH3:54])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 10604917HCID 10604917, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 21996667HCID 21996667, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60%, 0.273 g, 6.84 mmol), 33 (2.24 g, 3.11 mmol), and 1-iodopropane (0.67 mL, 6.9 mmol) in DMF (30 mL) were combined and worked up by the method of 43. Column chromatography (3:1 hexane/EtOAc) provided 2.01 g (80%) of 54 as an oil: NMR δ 0.71-0.78 (m, 6 H), 1.01-1.11 (m, 2 H), 1.34-1.48 (m, 12 H), 2.29 (s, 6 H), 2.57-2.58 (2 s, 18 H), 2.98-3.13 (m, 12 H), 6.92 (s, 6 H). Anal. (C42H65N3O6S3.H2O) C, H, N.

Sources & evidence

ORD record
ord-a02388ebf6e0485fa4fc3184746256a3
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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