Triphenylphosphine → methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

HRID 392310

Reaction equation

HRID 392310 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[C:14]2=[O:23])[O:4]1.[P:24]([O-])([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>N1C=CC=CC=1>[CH2:27]([O:26][P:24]([O:1][CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[C:14]2=[O:23])[O:4]1)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 4193600DibenzylphosphateHCID 60126642HCID 60126642, compound

Product 1

HCID 69759751methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylateYield 102.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 4 mL of pyridine was dissolved 0.22 g of methyl 4-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. Then, 0.17 g of dibenzyl phosphate, 0.40 g of triphenylphosphine and 0.30 mL of diisopropyl azodicarboxylate were successively added and stirred at room temperature for 15 hours, and the solvent was removed under reduced pressure. By purifying the residue by column chromatography [eluent: ethyl acetate], 0.37 g of methyl 4-[(3aR,4R,6R,6aR)-6-({[bis(benzyloxy)phosphoryl]oxy}methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate was obtained as an orange-colored solid product.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customBy purifying the residue by column chromatography [eluent: ethyl acetate]

Sources & evidence

ORD record
ord-93e88e7c6186441da570a7c73aa12fcd
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Linked notes

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