(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627136

Reaction equation

HRID 627136 reaction equation
C(O[N:5]([C@H]1CN(C(OC(C)(C)C)=O)[C@H](C(=O)N)C(C)=C1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C.[CH2:35]([O:38][N:39]([C@H:52]1[CH2:57][N:56]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:55]([C:65]([OH:67])=O)[C:54]([CH:68]([CH3:70])[CH3:69])=[CH:53]1)[S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[N+:49]([O-:51])=[O:50])(=[O:42])=[O:41])[CH:36]=[CH2:37]>>[CH2:35]([O:38][N:39]([C@H:52]1[CH2:57][N:56]([C:58]([O:60][C:61]([CH3:63])([CH3:64])[CH3:62])=[O:59])[C@H:55]([C:65](=[O:67])[NH2:5])[C:54]([CH:68]([CH3:70])[CH3:69])=[CH:53]1)[S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[N+:49]([O-:51])=[O:50])(=[O:41])=[O:42])[CH:36]=[CH2:37]

Participants

3

Reactant 2

HCID 89852135(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid2×HCID 89852450(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852417(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylateYield 43.7%

Procedure

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate (0.260 g, 43.7%) was prepared a similar manner as described in Intermediate 83 as a pale yellow oil, using (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-3-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid (Intermediate 93, 0.595 g, 1.13 mmol) as a starting material.

Sources & evidence

ORD record
ord-fae6d740e3394e9c926503d0615a2fbd
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Linked notes

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