Triphenylphosphine → HCID 66756812, compound

HRID 1642601Notes

Reaction equation

HRID 1642601 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. After it is stirred for 50 min., 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 out 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. customtoluene 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 out
  6. concentrationthe filtrate is then concentrated
  7. customThe residue is then purified by column chromatography

Sources & evidence

ORD record
ord-c62f5c376ee74c16b4d4bc517ed018ca
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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