2-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627250Notes

Reaction equation

HRID 627250 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH:16]2[CH2:18][CH2:17]2)=[CH:14][C@H:13](O)[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:27]([O:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[CH:28]=[CH2:29].C(ON([C@H]1CN(C(OC(C)(C)C)=O)[C@H](CO[Si](C(C)(C)C)(C)C)C=C1C)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:27]([O:30][N:31]([C@H:13]1[CH2:12][N:11]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[C:15]([CH:16]2[CH2:17][CH2:18]2)=[CH:14]1)[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[CH:28]=[CH2:29]

Participants

4

Reactant 3

HCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide2×HCID 89852394(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate2×HCID 89852484(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 131735296(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 238, 2.74 g, 7.14 mmol) and N-(allyloxy)-2-nitrobenzenesulfonamide (Intermediate 9, 1.85 g, 7.14 mmol) following the procedure described for Intermediate 10. The desired product was obtained as a light yellow oil (3.19 g, 71%).

Sources & evidence

ORD record
ord-fc1313fe68f2447194b1963458ceac83
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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