Sodium hydride → HCID 10843119, compound

HRID 1978300Notes

Reaction equation

HRID 1978300 reaction equation
[H-].[Na+].[C:3]1([CH3:51])[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][CH2:19][N:20]([S:39]([C:42]1[C:47]([CH3:48])=[CH:46][C:45]([CH3:49])=[CH:44][C:43]=1[CH3:50])(=[O:41])=[O:40])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([C:30]1[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=1[CH3:38])(=[O:29])=[O:28])(=[O:13])=[O:12].I[CH2:53][CH2:54][CH3:55].[CH3:56][CH2:57][CH2:58]CCC.CCOC(C)=O>CN(C=O)C>[C:5]1([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH3:51])[C:4]=1[S:11]([N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]([S:39]([C:42]1[C:43]([CH3:50])=[CH:44][C:45]([CH3:49])=[CH:46][C:47]=1[CH3:48])(=[O:40])=[O:41])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([S:27]([C:30]1[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=1[CH3:36])(=[O:28])=[O:29])[CH2:56][CH2:57][CH3:58])[CH2:53][CH2:54][CH3:55])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 10771258HCID 10771258, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10843119HCID 10843119, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (80%, 198 mg, 6.6 mmol), 34 (1.51 g, 2.06 mmol), and 1-iodopropane (0.44 mL, 4.5 mmol) in DMF (40 mL) were reacted and worked up by the method of 43. Column chromatography (7:2/hexane/EtOAc) provided 1.61 g (95%) of 57 as an oil: NMR δ 0.75 (t, 6 H, J=7), 1.02-1.14 (m, 4 H), 1.36-1.52 (m, 12 H), 2.30 (s, 9 H), 2.60 (s, 18 H), 3.02-3.16 (m, 12 H), 6.95 (s, 6 H). Anal. (C43H67N3O6S3) C, H, N.

Sources & evidence

ORD record
ord-424357e57b7a4bc79b85c35f3e229975
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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