Triphenylphosphine → HCID 21356675, compound

HRID 1167426Notes

Reaction equation

HRID 1167426 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH2:4]1.CSC1C=CC(N)=CC=1.C(OC[C@@H]1OC1)(=O)CCC.O[C:37]1[CH:41]=[CH:40][O:39][N:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:39]1[CH:40]=[CH:41][C:37]([O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=3)[CH2:4]2)=[N:38]1

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 660384-(Methylthio)anilineHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 5363146Diisopropyl azodicarboxylateHCID 13038084(5R)-5-(Hydroxymethyl)-3-[4-(methylsulfanyl)phenyl]-1,3-oxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 21356675HCID 21356675, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared by the general method of Example 1 using 5(R)-hydroxymethyl-3-(4-methylthiophenyl)oxazolidin-2-one (650 mg, 2.72 mmol ; prepared from the reaction of 4-methylthioaniline and (R)-glycidyl butyrate), 3-hydroxyisoxazole (243 mg, 2.86 mmol), diisopropylazodicarboxylate (577 mg, 2.86 mmol) and triphenylphosphine (770 mg, 2.94 mmol) in THF (10 ml). Purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (1/1)) to give the title compound 507 mg, 61%) as a colourless solid. MS: ESP+ (M+H)+=307.

Workup

  1. customPurified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (1/1))

Sources & evidence

ORD record
ord-135f7bfe193c4304a4d484e8fe69ad0c
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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