(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627133Notes

Reaction equation

HRID 627133 reaction equation
[CH2:1]([O:4][N:5]([C@H]1CN(C(OC(C)(C)C)=O)[C@H](CO[Si](C(C)(C)C)(C)C)C(C)=C1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].[Si:41]([O:48][CH2:49][C@@H:50]1[C:55]([CH:56]([CH3:58])[CH3:57])=[CH:54][C@H:53](O)[CH2:52][N:51]1[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]>>[CH2:1]([O:4][N:5]([C@H:53]1[CH2:52][N:51]([C:60]([O:62][C:63]([CH3:65])([CH3:64])[CH3:66])=[O:61])[C@H:50]([CH2:49][O:48][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:42])[CH3:43])[C:55]([CH:56]([CH3:58])[CH3:57])=[CH:54]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89852247(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 89852556(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852426(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylateYield 78%

Procedure

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate (0.928 g, 78%) was prepared as described in Intermediate 80 as a pale yellow oil, using (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 90, 0.731 g, 1.90 mmol) as a starting material.

Sources & evidence

ORD record
ord-7a615a932c7147e0ae2d84a8b0b41bcb
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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