Methylparaben → HCID 67405696, compound

HRID 1372589Notes

Reaction equation

HRID 1372589 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]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][C@H:23]1[CH2:34][OH:35])=[O:21])([CH3:18])([CH3:17])[CH3:16].O[C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=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:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:24][C@H:23]1[CH2:34][O:35][C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59838273HCID 59838273, compound

Product 1

HCID 67405696HCID 67405696, compoundYield 149%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (0.64 ml, 3.25 mmol) was added dropwise while stirring a mixture of (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylmethanol (1.16 g, 3.25 mmol), methyl 4-hydoxybenzoate (494 mg, 3.25 mmol) and triphenylphosphine (852 mg, 3.25 mmol) in THF (30 ml) at room temperature in a nitrogen gas stream. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 20 minutes and at 80° C. for 8 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (silica gel: 200 g), whereby from chloroform/acetone (20/1) eluate fractions, the title compound (2.07 g, 100%) was obtained as a colorless oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe reaction mixture was stirred at room temperature for 20 minutes and at 80° C. for 8 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (silica gel: 200 g), whereby from chloroform/acetone (20/1) eluate fractions

Sources & evidence

ORD record
ord-8c49a90761e5413496d8278bdea214a9
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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