Methanol → HCID 66590129, compound

HRID 1092802Notes

Reaction equation

HRID 1092802 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:15]([CH2:21][C:22]([N:24]([CH:34]1[CH2:36][CH2:35]1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[Cl:33])=[O:23])[CH2:16][O:17][CH2:18][O:19][CH3:20])[CH2:9][CH2:10][C:11](OC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].CO.[Cl-].[NH4+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:34]1([N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])[C:22]([CH:21]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@@H:15]2[CH2:16][O:17][CH2:18][O:19][CH3:20])=[O:23])[CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 66596155HCID 66596155, compound

Product 1

HCID 66590129HCID 66590129, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 100 mL round bottom flask was added 4E and toluene (42 mL) under nitrogen. Sodium metal (392 mg, 17.1 mmol, 1.3 eq) was added at once followed by methanol (160 μL, 3.9 mmol, 0.3 eq). The reaction was allowed to stir under nitrogen over 48 hours. After sodium metal had dissolved, saturated ammonium chloride (50 mL) was added to quench the reaction. Ethyl acetate (50 mL) was added and the mixture was transferred to a separatory funnel. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×50 mL). The organic layers were combined and dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave a residue which was purified by column chromatography (20% ethyl acetate/hexanes) to give 4F (4.17 g, 62%). ESI-MS:m/z 459.3 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe mixture was transferred to a separatory funnel
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted with ethyl acetate (2×50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customSolvent was removed under vacuum
  9. customto leave a residue which
  10. customwas purified by column chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-01bd5e5ed8014b2fb790b9d84673ea1f
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

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