tert-Butyl methyl ether → HCID 58781014, compound

HRID 1373162Notes

Reaction equation

HRID 1373162 reaction equation
[H-].[Na+].[OH:3][C@H:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[CH2:5]1.I[C:24]1[NH:25][C:26](C)([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[O:27][C:28]=1[CH3:29].[C:41](OC)(C)(C)C>CN(C)C=O>[CH3:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:12]([CH2:11][O:10][C@@H:6]2[CH2:7][CH2:8][CH2:9][C@H:4]([O:3][CH2:41][C:24]3[N:25]=[C:26]([C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:31]=4)[O:27][C:28]=3[CH3:29])[CH2:5]2)[C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 11492838methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoateHCID 69494645HCID 69494645, compound

Product 1

HCID 58781014HCID 58781014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 50 mg of a 60% strength suspension of sodium hydride are added to a solution of 200 mg of methyl 2-((1R,3S)-3-hydroxycyclohexyloxy-methyl)-6-methylbenzoate in 5 ml of dimethylformamide, and 380 mg of 4-iodo-methyl-5-methyl-2-naphthalen-2-yloxazole are then added. After one hour, methyl tert-butyl ether is added and the mixture is extracted with water. The organic phase is dried over magnesium sulfate, the solvents are removed under reduced pressure and the residue is purified by RP-HPLC. This gives 94 mg of methyl 2-methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-ylmethoxy)cyclohexyl-oxymethyl]benzoate as a light-yellow oil.

Workup

  1. additionare then added
  2. extractionthe mixture is extracted with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvents are removed under reduced pressure
  5. customthe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-4ecf459d670d4304a72dc9ff93c37568
Source dataset
uspto-grants-2007_01
Patent number
US07160911B2

Reaction notes

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