Triphenylphosphine → HCID 10069254, compound

HRID 1452599Notes

Reaction equation

HRID 1452599 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][C@@H:17]([CH2:19]CO)[O:16][C:15]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:43][C:44]1[NH:48][N:47]=[N:46][N:45]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl.C(OCC)(=O)C.CO>[S:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][N:46]4[N:47]=[N:48][C:44]([CH3:43])=[N:45]4)[O:16][C:15]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68880499HCID 68880499, compound2×HCID 178434708HCID 178434708, compound

Product 1

HCID 10069254HCID 10069254, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-3-[4-(Tetrahydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(hydroxymethyl)methyl]oxazolidin-2-one (Intermediate 47) (0.66 g, 2 mmol), triphenylphosphine (0.786 g, 3 mmol), 5-methyl tetrazole (0.303 g, 3.6 mmol) and diisopropylazodicarboxylate (0.59 ml, 3 mmol) were reacted as described for Example 28. Chromatography on silica gel with 0.2-0.5% methanol in dichloromethane followed by 40% ethyl acetate in hexanes gave the title product (0.412 g).

Sources & evidence

ORD record
ord-fd2e4df91a9247c088f4bb20e78127b0
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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