Triphenylphosphine → tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate

HRID 2277164Notes

Reaction equation

HRID 2277164 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([OH:11])[CH:3]=1.O[CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([O:11][CH2:15][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 66880968DIAD tolueneHCID 178526833HCID 178526833, compound

Product 1

HCID 86731217tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamateYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5-nitropyridin-2-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.51 g) and triphenylphosphine (2.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.52 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (860 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e74d8aefbfc34a3b96417dba1ee9428c
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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