Methanol → HCID 67170182, compound

HRID 1475701Notes

Reaction equation

HRID 1475701 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13]([C:15]1([NH:22][C:23](=[O:42])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][C:35]3[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=3)[CH:25]=2)[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)=[O:14].[CH3:43]O.P([O-])(O)(O)=O.[Na+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:11][O:12][C:13]([C:15]1([NH:22][C:23](=[O:42])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][C:35]3[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=3)[CH:25]=2)[CH2:20][CH2:19][C:18](=[CH2:43])[CH2:17][CH2:16]1)=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 23672064Monosodium phosphateHCID 67170651HCID 67170651, compound

Product 1

HCID 67170182HCID 67170182, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyltriphenylphosphonium bromide (4.88 g, 13.7 mmol) was suspended in THF. Potassium bis(trimethylsilyl)amide (13.6 mmol, solution in toluene) was added slowly and the mixture was stirred at room temperature for 1 h. The mixture was cooled in a acetone/dry ice bath and the compound of step 1 of example 55 (3.00 g, 6.83 mmol) was added. The mixture was warmed to room temperature and stirred overnight. Methanol and an aqueous sodium dihydrogenphosphate solution were added. The mixture was extracted with diethyl ether, the combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield the title compound (1.40 g).

Workup

  1. temperatureThe mixture was cooled in a acetone/dry ice bath
  2. temperatureThe mixture was warmed to room temperature
  3. stirringstirred overnight
  4. extractionThe mixture was extracted with diethyl ether
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-36bfdcee1afb4320844672e94ff0caeb
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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