Phenol → HCID 10710901, compound

HRID 1372586Notes

Reaction equation

HRID 1372586 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([OH:27])[CH2:24][C@H:23]1[C:28]([O:30][CH3:31])=[O:29])=[O:21])([CH3:18])([CH3:17])[CH3:16].[C:32]1(O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([O:27][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][C@H:23]1[C:28]([O:30][CH3:31])=[O:29])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 10710901HCID 10710901, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (4.13 ml, 21.0 mmol) was added to a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarboxylate (4.69 g, 19.1 mmol), phenol (1.98 g, 21.0 mmol) and triphenylphosphine (5.51 g, 21.0 mmol) in THF (80 ml) under stirring at room temperature in a nitrogen gas stream. The reaction mixture was stirred overnight at room temperature. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by chromatography on a silica gel column (silica gel: 700 g), whereby from chloroform/ethyl acetate (10/1) eluate fractions, the title compound (5.31 mg, 86%) was obtained as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. customwas purified by chromatography on a silica gel column (silica gel: 700 g), whereby from chloroform/ethyl acetate (10/1) eluate fractions

Sources & evidence

ORD record
ord-12788d22f7ce4e2984a339aef37ff8c2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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