Triphenylphosphine → HCID 87285738, compound

HRID 574248Notes

Reaction equation

HRID 574248 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](=[O:14])[NH:7][C:6]1=[O:15].[C:21]([O:25][C:26](=[O:37])[NH:27][C@H:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:29]O)([CH3:24])([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:21]([O:25][C:26](=[O:37])[NH:27][C@H:28]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:29][N:7]1[C:8](=[O:14])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]([CH2:4][C:3]2[C:2]([F:1])=[CH:19][CH:18]=[CH:17][C:16]=2[F:20])[C:6]1=[O:15])([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl esterHCID 247573541-(2,6-difluoro-benzyl)-5-nitro-1H-pyrimidine-2,4-dione

Product 1

HCID 87285738HCID 87285738, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,6-difluoro-benzyl)-5-nitro-1H-pyrimidine-2,4-dione (82 mg, 0.29 mmol), ((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (69 mg, 0.29 mmol), and triphenylphosphine (114 mg, 0.44 mmol) were dissolved in anhydrous tetrahydrofuran (2 mL). To this solution was added diethyl azodicarboxylate (200 μl, 0.44 mmol), followed by stirring at room temperature for 4 hrs. The solution was concentrated, after which the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 3/1/1) and dried in a vacuum to afford 67 mg of the compound as a colorless oil (yield 67%). 1H NMR (300 MHz, CDCl3) δ 1.30 (9H, s), 3.40 (1H, d), 4.50 (1H, m), 5.08-5.27 (4H, m), 7.02 (2H, t), 7.26-7.47 (6H, m), 8.78 (1H, s)

Workup

  1. concentrationThe solution was concentrated
  2. customafter which the residue was purified
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-ed4a59c3fa0f4e62a077c3689ed2d951
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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