Triphenylphosphine → HCID 18665557, compound

HRID 2395388Notes

Reaction equation

HRID 2395388 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:27])=[C:11]([CH:24]=[CH:25][CH:26]=1)[C:12]([NH:14][CH2:15][C@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)O)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Si:1]([O:8][C:9]1[C:10]([F:27])=[C:11]([C:12]2[O:13][C@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][N:14]=2)[CH:24]=[CH:25][CH:26]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18665556HCID 18665556, compound

Product 1

HCID 18665557HCID 18665557, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-tert-butyldimethylsilyloxy-2-fluorobenzamido)-1(S)-phenylethanol (4.6 g, 12 mmol) and triphenylphosphine (3.7 g, 14 mmol) in THF (50 ml) was added dropwise a solution of diethyl azodicarboxylate (2.2 ml, 42 mmol) in THF (20 ml). After stirring for 1 h, volatiles were removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (13:1 to 9:1) to afford the title compound (2.2 g, 50%) as a pale yellow liquid.

Workup

  1. customvolatiles were removed by evaporation
  2. customThe residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (13:1 to 9:1)

Sources & evidence

ORD record
ord-2e22cad8330f4f17ba4c353d6cb194fa
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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