3-Chlorophenol → HCID 86633188, compound

HRID 1160466Notes

Reaction equation

HRID 1160466 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11].[Cl:18][C:19]1[CH:20]=[C:21](O)[CH:22]=[CH:23][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([O:9][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:18])[CH:24]=2)[CH2:6][N:5]1[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11]

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68030591HCID 68030591, compound

Product 1

HCID 86633188HCID 86633188, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-α-butoxycarbonyl-cis-4-hydroxy-L-proline methylester 123 mg (0.50 mmol), 3-chlorophenol 0.058 ml (0.55 mmol), triphenylphosphine 184 mg (0.70 mmol) and tetrahydrofuran 2 ml was added diisopropyl azodicarboxylate 0.150 ml (0.75 mmol) dropwise under ice-cooling and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated and the residue was purified by a column chromatography on silica gel (eluted with a mixed solvent of ethyl acetate and hexane) to give 155 mg (0.44 mmol) of the title compound (yield: 87%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified by a column chromatography on silica gel (
  4. washeluted with a mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-075a516861be476aa5cb99580614c8b6
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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