Triphenylphosphine → HCID 68325460, compound

HRID 571850Notes

Reaction equation

HRID 571850 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[CH2:9][N:10]([CH2:18][CH2:19]O)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([F:22])[CH:3]=1.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>CC(OC)(C)C>[C:13]([O:12][C:11]([N:10]1[CH2:18][CH2:19][O:21][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:22])[CH2:9]1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68325867HCID 68325867, compound

Product 1

HCID 68325460HCID 68325460, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Under N2, tert-butyl 2-(4-bromo-2-fluoro-phenyl)-2-hydroxyethyl(2-hydroxyethyl)carbamate (7.385 g, 19.5 mmol, Eq: 1.00) and triphenylphosphine (6.15 g, 23.4 mmol, Eq: 1.2) were dissolved in TBME (33 ml). Under ice-bath cooling, DIAD (5.04 g, 4.85 ml, 23.4 mmol, Eq: 1.2) was added (exotherm). The yellow solution was stirred at RT overnight. The RM became a yellow suspension. Control with TLC: the reaction was finished. The solvent was evaporated. TBME was added and the solid was filtered. The filtrate was evaporated. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 40% EtOAc in heptane).

Workup

  1. temperatureUnder ice-bath cooling
  2. customThe solvent was evaporated
  3. additionTBME was added
  4. filtrationthe solid was filtered
  5. customThe filtrate was evaporated
  6. customThe crude material was purified by flash chromatography (silica gel, 100 g, 5% to 40% EtOAc in heptane)

Sources & evidence

ORD record
ord-6434ccb816c94c9db179338febdb0b48
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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