N,N,N',N',N'',N''-Hexamethylmethanetriamine → (S)-5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

HRID 30496

Reaction equation

HRID 30496 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:21])[O:8][C@@:9]([C:14](=[O:20])[N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])([CH2:12][CH3:13])[C:10]=1[CH3:11])=[O:5])[CH3:2].C[C@H]1C[C@@H](OC(=O)C(=O)CC)[C@H](C(C)(C2C=CC=CC=2)C)CC1.[CH3:45][N:46]([CH:48](N(C)C)N(C)C)[CH3:47]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:21])[O:8][C@@:9]([C:14](=[O:20])[N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])([CH2:12][CH3:13])[C:10]=1/[CH:11]=[CH:45]/[N:46]([CH3:48])[CH3:47])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 110883962-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl esterHCID 11687992(S)-5-diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Product 1

HCID 11523197(S)-5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the procedure described in Example 6 1.22 0 g of compound (23) as obtained from example 17 (4.103 mmol) in 7.3 mL dimethyl formamide were treated with 7.55 mL tris(dimethylamino)methane (42.26 mmol, 10.3 eq) yielding the crude product as an orange oil (1.463 mg, 101% by weight).

Sources & evidence

ORD record
ord-bbd7d798654d40d2a16d1a5d7de0ddf3
Source dataset
uspto-grants-2008_09
Patent number
US07423152B2

Linked notes

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