methyl 4-(tert-butoxycarbonyl((S)-1-methoxybut-3-en-2-yl)amino)-3-hydroxy-2-methylenebutanoate → (2S,5S)-1-tert-butyl 4-methyl 5-hydroxy-2-(methoxymethyl)-5,6-dihydropyridine-1,4(2H)-dicarboxylate

HRID 627263

Reaction equation

HRID 627263 reaction equation
[Si](OC[C@@H]1C=C(C(OC)=O)[C@H](O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C.[C:28]([O:32][C:33]([N:35]([C@@H:45]([CH:49]=C)[CH2:46][O:47][CH3:48])[CH2:36][CH:37]([OH:44])[C:38](=C)[C:39]([O:41][CH3:42])=[O:40])=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[OH:44][C@@H:37]1[CH2:36][N:35]([C:33]([O:32][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:34])[C@H:45]([CH2:46][O:47][CH3:48])[CH:49]=[C:38]1[C:39]([O:41][CH3:42])=[O:40]

Participants

3

Reactant 2

HCID 89851376methyl 4-(tert-butoxycarbonyl((S)-1-methoxybut-3-en-2-yl)amino)-3-hydroxy-2-methylenebutanoate2×HCID 89852366(2S,5S)-1-tert-butyl 4-methyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1,4(2H)-dicarboxylate

Product 1

HCID 89852057(2S,5S)-1-tert-butyl 4-methyl 5-hydroxy-2-(methoxymethyl)-5,6-dihydropyridine-1,4(2H)-dicarboxylateYield 40.3%

Procedure

The title compound (0.45 g, 40%) was prepared according to the procedure described for Intermediate 101 starting from methyl 4-(tert-butoxycarbonyl((S)-1-methoxybut-3-en-2-yl)amino)-3-hydroxy-2-methylenebutanoate (Intermediate 253, 1.22 g).

Sources & evidence

ORD record
ord-a76f167e9da14ddcaafa528882978aa1
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Linked notes

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