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

HRID 627126Notes

Reaction equation

HRID 627126 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C:15]([CH3:16])=[CH:14][C@H:13](O)[CH2:12][N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:25]([O:28][NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:32])=[O:31])[CH:26]=[CH2:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:25]([O:28][N:29]([C@H:13]1[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3])[C:15]([CH3:16])=[CH:14]1)[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:32])=[O:31])[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamideHCID 89852311HCID 89852311, compound2×

Product 1

HCID 89852556(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 79, 5.48 g, 15.33 mmol), N-(allyloxy)-2-nitrobenzenesulfonamide (7.92 g, 30.65 mmol) and triphenylphosphine (12.06 g, 45.98 mmol) in toluene (20 mL) was cooled in an ice-bath and added dropwise (E)-diisopropyl diazene-1,2-dicarboxylate (8.91 ml, 45.98 mmol). Reaction was let warm up to rt and continued to stir at rt for 2 h. The reaction mixture was evaporated and the crude product was loaded onto silica gel, purified via flash chromatography (750 g, 0-50%) to obtain the desired product (7.05 g, 77%) as a yellow oil.

Workup

  1. temperaturewas cooled in an ice-bath
  2. customReaction
  3. customThe reaction mixture was evaporated
  4. custompurified via flash chromatography (750 g, 0-50%)

Sources & evidence

ORD record
ord-b5b251a275e5440bb0102ed0a46f5310
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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