Triphenylphosphine → HCID 67449728, compound

HRID 1019831Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.O[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:21]([O:20][C:19]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][O:12][C:4]1[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[O:25])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: -10 °C

Procedure

Methyl 4-fluoro-2-hydroxybenzoate (21 mmol), tert-butyl 4-hydroxybutylcarbamate (21 mmol) and triphenyl phosphine (24 mmol) in THF (70 ml) was cooled to −10° C. Then, DIAD (43 mmol) was added. The mixture was stirred for 30 min at −10° C. under N2. The ice-bath was removed and the mixture was stirred overnight at 20° C. The solvent was removed under vacuum. The residue was washed with petroleum and diethyl ether. The white solid was filtered and it was confirmed to be triphenylphosphine oxide (PPh3═O). The filtrate was evaporated to dryness. The residue was purified with flash column (petroleum/ethyl acetate 100:0 to 5:1). Yield: 8.18 g (purity 90%, yield 98%).

Workup

customThe ice-bath was removed
stirringthe mixture was stirred overnight at 20° C
customThe solvent was removed under vacuum
washThe residue was washed with petroleum and diethyl ether
filtrationThe white solid was filtered
customThe filtrate was evaporated to dryness
customThe residue was purified with flash column (petroleum/ethyl acetate 100:0 to 5:1)

Sources & evidence

ORD record: ord-b8ee206263e3465797769fc18cedfdcf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716293B2

Reaction notes

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