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

HRID 627145Notes

Reaction equation

HRID 627145 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][Si](C(C)(C)C)(C)C)[CH:20]=[C:19]1[C:40](=[O:42])[NH2:41])[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].C(ON1C(=O)N2C[C@H]1C(C(N)=O)=C[C@H]2CO)C=C.C(ON1C(=O)N2C[C@H]1C(C(N)=O)=C[C@H]2CO[Si](C(C)(C)C)(C)C)C=C>>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C@H:21]([CH2:31][OH:32])[CH:20]=[C:19]1[C:40](=[O:42])[NH2:41])[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

4

Reactant 3

HCID 89852378(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 89852439(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamideHCID 89854131(2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

Product 1

HCID 89852519(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-carbamoyl-2-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylateYield 67%

Procedure

The title compound (617 mg, 67%) was prepared from (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 110, 1.2 g, 1.80 mmol) using the same procedure to prepare Intermediate 109 from Intermediate 108.

Sources & evidence

ORD record
ord-f5596f39bcd34bdbb9f931a8ff693efe
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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