Sodium hydride → HCID 10795483, compound

HRID 1978304Notes

Reaction equation

HRID 1978304 reaction equation
[H-].[Na+].BrC[CH2:5][CH2:6][CH2:7][N:8]([CH2:21][CH2:22]C)[S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:11])=[O:10].[C:24]1([CH3:79])[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[S:32]([N:35]([CH2:60][CH2:61]CN(S(C1C(C)=CC(C)=CC=1C)(=O)=O)CCC)[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:34])=[O:33].C1(C)C=CC=CC=1.CCOC(C)=O>CN(C=O)C>[C:24]1([CH3:79])[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[S:32]([N:35]([CH2:60][CH2:61][CH2:22][CH2:21][N:8]([S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:10])=[O:11])[CH2:7][CH2:6][CH3:5])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:33])=[O:34]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 10499756HCID 10499756, compoundHCID 10629120HCID 10629120, compoundHCID 21584019Toluene ethylacetate

Product 1

HCID 10795483HCID 10795483, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60%, 0.12 g, 2.90 mmol), 71 (1.24 g, 2.42 mmol) in DMF (30 mL), and 67 (0.91 g, 2.42 mmol) in DMF (10 mL) were reacted and worked up following the method of 72. Column chromatography (25:1 toluene/EtOAc) gave 1.67 g (85%) of 74 as an oil: NMR δ 0.74 (t, 3 H, J=7), 1.35-1.45 (m, 11 H), 2.00 (t, 2 H, J=7), 2.25 (s, 3 H), 2.28 (s, 3 H), 2.55 (s, 6 H), 2.56 (s, 6 H), 2.98-3.08 (m, 8 H), 6.90 (s, 2 H), 6.91 (s, 2 H), 7.15-7.44 (m, 15 H). Anal. (C48H61N3O4S2) C, H, N.

Sources & evidence

ORD record
ord-3df5eef7572f47e08cf42bb6ad474667
Source dataset
uspto-grants-2001_05
Patent number
US06235794B1

Reaction notes

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