Triphenylphosphine → HCID 18634268, compound

HRID 1722270Notes

Reaction equation

HRID 1722270 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:20]1[C@@H:24]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:23]([CH2:32][CH2:33]O)[O:22][C:21]1([CH3:36])[CH3:35])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br-:56].[NH+]1C=CC=CC=1>C(Cl)Cl.O>[C:13]([N:20]1[C@@H:24]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:23]([CH2:32][CH2:33][Br:56])[O:22][C:21]1([CH3:36])[CH3:35])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11309665Pyridinium bromideHCID 18634269HCID 18634269, compound

Product 1

HCID 18634268HCID 18634268, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.6 ml of diethyl azodicarboxylate are added dropwise, at 20° C. under argon, to 690 mg of 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5-(2-hydroxyethyl)oxazolidine, 2.6 g of triphenylphosphine and 1.6 g of pyridinium bromide in 15 ml of CH2Cl2. After 16 h at R.T., H2O is added and the mixture is diluted with 100 ml of CH2Cl2. The organic phase is washed twice with saturated NaHCO3 solution and once with saturated NaCl solution. The organic phase is dried with Na2SO4 and concentrated, and the residue is taken up in a little EA and filtered to remove PPh3. Purification on silica gel provides the title compound (eluent: H/EA 15:1).

Workup

  1. washThe organic phase is washed twice with saturated NaHCO3 solution and once with saturated NaCl solution
  2. dry with materialThe organic phase is dried with Na2SO4
  3. concentrationconcentrated
  4. filtrationfiltered
  5. customto remove PPh3
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-039dd923b5b949f596afb454a72b2464
Source dataset
uspto-grants-1989_08
Patent number
US04855286

Reaction notes

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