Triphenylphosphine → HCID 66756812, compound

HRID 660476Notes

Reaction equation

HRID 660476 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][N:8]([S:24](=[O:34])(=[O:33])[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:55][Si:56]([CH3:61])([CH3:60])[CH2:57][CH2:58]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:10]1[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=1[N:8]([S:24]([N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:58][CH2:57][Si:56]([CH3:61])([CH3:60])[CH3:55])(=[O:33])=[O:34])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:35])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 180132-(Trimethylsilyl)ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 66756685HCID 66756685, compound

Product 1

HCID 66756812HCID 66756812, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-iodophenyl)glycine tert-butyl ester (3.49 g, 5.6 mmol) in toluene (224 mL) is added triphenylphosphine (2.22 g, 8.47 mmol) and 2-trimethylsilanylethanol (992 mg, 8.38 mmol). DIAD (1.6 mL, 8.13 mmol) is then added dropwise over 10 min. The mixture is stirred for 50 min then the toluene is remove under reduced pressure. After 18 h, 20% EtOAc/hexane is added (50 ml in 4 increments) to form a precipitate. The solid is filtered and the filtrate is then concentrated. The residue is then purified by column chromatography to give the title compound as a white foam.

Workup

  1. customthe toluene is remove under reduced pressure
  2. waitAfter 18 h
  3. addition20% EtOAc/hexane is added (50 ml in 4 increments)
  4. customto form a precipitate
  5. filtrationThe solid is filtered
  6. concentrationthe filtrate is then concentrated
  7. customThe residue is then purified by column chromatography

Sources & evidence

ORD record
ord-742bea5ac1894e078163b88eb6cf379b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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