tert-Butanol → HCID 68541748, compound

HRID 1432097Notes

Reaction equation

HRID 1432097 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH:16]1[CH2:20][CH2:19][C:18](=[O:21])[O:17]1)[CH2:9][CH:10]([CH3:15])[CH2:11][CH2:12][CH:13]=[O:14])([CH3:4])([CH3:3])[CH3:2].CC([OH:27])(C)C.CC(=CC)C.[O-]Cl=O.[Na+]>CCOC(C)=O.[Cl-].[Na+].O.C1COCC1.O>[C:1]([O:5][C:6]([NH:7][CH:8]([CH:16]1[CH2:20][CH2:19][C:18](=[O:21])[O:17]1)[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][C:13]([OH:27])=[O:14])=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 4

HCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86611582HCID 86611582, compound

Product 1

HCID 68541748HCID 68541748, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2.09 g (6.67 mmol) [(R)-3-Methyl-6-oxo-1-(5-oxo-tetrahydro-furan-2-yl)-hexyl]-carbamic acid tert-butyl ester, 1.2 g (10 mol) NaH2PO4, 50 ml tBuOH and 10 ml water is subsequently treated with 20 ml of a 2M THF solution of 2-methyl-2-butene and 2.35 g (20.6 mmol) NaClO2 (technical, 80%). After stirring for 10 min the mixture is diluted with EtOAc and brine. The organic phase is dried with MgSO4, filtered and evaporated to yield the title compound as a resin which is used in the next step without purification.

Workup

  1. dry with materialThe organic phase is dried with MgSO4
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-cf2a7350e4c145b8bbc9baa7b120a78f
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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