2-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide → (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)-oxy)methyl)-4-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627191Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:13](=O)[CH2:12][N:11]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H]1C=C(COCC2C=CC(OC)=CC=2)C(O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C.[CH2:69]([O:72][NH:73][S:74]([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=1[N+:83]([O-:85])=[O:84])(=[O:76])=[O:75])[CH:70]=[CH2:71].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>>[CH2:69]([O:72][N:73]([CH:13]1[CH2:12][N:11]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:15]=[C:14]1[CH2:16][O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[S:74]([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=1[N+:83]([O-:85])=[O:84])(=[O:76])=[O:75])[CH:70]=[CH2:71]

Participants

Reactant 4

HCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide2×

HCID 89852314(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((4-methoxybenzyl)-oxy)methyl)-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate

HCID 89852484(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate

HCID 131735286(2S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-4-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89851796(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(((tert-butyldimethylsilyl)-oxy)methyl)-4-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((4-methoxybenzyl)-oxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 169, 17.10 g, 34.78 mmol) and N-(allyloxy)-2-nitrobenzenesulfonamide (Intermediate 9, 9.88 g, 38.26 mmol) according to the procedure described for Intermediate 10. Desired product was obtained as a pale yellow oil, 18.70 g, 74%.

Sources & evidence

ORD record: ord-f799703dc1cd4b2889074486ea970900
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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