Phenol → HCID 59908685, compound

HRID 393980Notes

Reaction equation

HRID 393980 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12])=[O:4].[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7061999HCID 7061999, compound

Product 1

HCID 59908685HCID 59908685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-Dimethoxybenzenesulfonyl)-[(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid] methyl ester (8) (1.00 g, 2.90 mmol), phenol (0.41 g, 4.34 mmol) and triphenylphosphine (1.14 g, 4.34) are combined in THF (10 mL). The mixture is cooled in an ice-bath and diethyl azodicarboxylate (0.76 g, 4.34 mmol) is added dropwise over 30 minutes. The reaction is allowed to warm to ambient temperature with overnight stirring. The reaction mixture is concentrated at reduced pressure and treated with ether. The mixture is decanted and the organic extract is concentrated. The residue is purified via silica gel chromatography (40% ethyl acetate in hexanes) affording the desired product as a solid. CIMS: MH+ 422

Workup

  1. temperatureThe mixture is cooled in an ice-bath
  2. concentrationThe reaction mixture is concentrated at reduced pressure
  3. additiontreated with ether
  4. customThe mixture is decanted
  5. extractionthe organic extract
  6. concentrationis concentrated
  7. customThe residue is purified via silica gel chromatography (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4122c08eb3f940a8ad59b885e92d73f2
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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