Phosphorus oxide (P4O10) → HCID 86600129, compound

HRID 271524Notes

Reaction equation

HRID 271524 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:40])[CH2:18][CH:19]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[C:33](=[N:37][O:38][CH3:39])[CH2:32][CH2:31]3)[C:20](=O)[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CS(O)(=O)=O>[CH3:39][O:38][N:37]=[C:33]1[C:34]2[C:30](=[CH:29][C:28]([C:19]3[CH:18]=[C:17]([CH:14]4[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]4)[O:40][C:20]=3[C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:36][CH:35]=2)[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 866001284-[3-(1-Methoxyimino-indan-5-yl)-4-oxo-4-pyridin-4-yl-butanoyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 86600129HCID 86600129, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

The product of Step 3 (3.0 g, 5.5 mmol) was added to a stirred suspension of phosphorus pentoxide (8 g) in dry methane sulphonic acid (50 ml). After stirring at room temperature for 4 hours the reaction mixture was cautiously poured into a stirred solution of ice cold 50% aqueous sodium hydroxide (final pH 10). The mixture was extracted with chloroform, washed with water and brine, dried and concentrated in vacuo and the residue purified by silica gel chromatography to give the title compound (0.66 g, 32%); MS(ES+) m/e 388 [M+H]+.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-0d345896a9194f259acc2f9731cdc511
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

Loading…