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

HRID 627150Notes

Reaction equation

HRID 627150 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[CH: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].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>[CH2:27]([O:30][N:31]([CH:13]1[CH2:12][N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH:15]=[C:14]1[CH2:16][O:17][CH3:18])[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

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 154979112-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamideHCID 89863076(2S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89863188(S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of Intermediate 118 (6.2 g, 16.00 mmol), N-(allyloxy)-2-nitrobenzenesulfonamide (4.34 g, 16.80 mmol) and triphenylphosphine (5.03 g, 19.20 mmol) in toluene (140 mL), was added (E)-diisopropyl diazene-1,2-dicarboxylate (3.67 g, 17.60 mmol) at rt. The reaction was stirred at rt over the weekend. The mixture was then concentrated and the residue was purified by silica gel column (120 g, 0-100% Hex/EA) to give the title compound (8.80 g, 88%) as an oil

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was purified by silica gel column (120 g, 0-100% Hex/EA)

Sources & evidence

ORD record
ord-ea081546e3824507a0e941abb12eb5b4
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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