Triphenylphosphine → HCID 18665572, compound

HRID 2395371Notes

Reaction equation

HRID 2395371 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9]([C:12]3[C:13]([F:22])=[C:14]([C:18]#[C:19][CH2:20]O)[CH:15]=[CH:16][CH:17]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([O:27][C:28]([NH:30][O:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:23]([O:27][C:28]([N:30]([CH2:20][C:19]#[C:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:9]2[O:10][CH2:11][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[C:13]=1[F:22])[O:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 18665558HCID 18665558, compound

Product 1

HCID 18665572HCID 18665572, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluorophenyl]-2-propyn-1-ol (1.41 g, 4.8 mmol), N,O-bis(tert-butoxycarbonyl)hydroxylamine (1.11 g, 4.8 mmol) and triphenylphosphine (1.63 g, 6.2 mmol) in dry tetrahydrofuran (350 ml) was added dropwise a solution of diethyl azodicarboxylate (1.08 g, 6.2 mmol) in dry tetrahydrofuran (15 ml). The reaction mixture was stirred for 2 hours and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:10) to afford N,O-di(tert-butoxycarbonyl)-[3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluoro-phenyl]-2-propyn-1-yl]hydroxylamine (1.64 g, 67%) as pale yellow plates.

Workup

  1. customvolatiles removed by evaporation
  2. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:10)

Sources & evidence

ORD record
ord-60763c2a998846a390f722b694a7b841
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

Loading…