tert-Butyl methyl ether → Methyl 2-{3-[2-(4-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoate

HRID 748013

Reaction equation

HRID 748013 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([CH2:15]I)[N:14]=2)=[CH:6][CH:5]=1.[OH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([O:25][CH2:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[C:28]=2[C:29]([O:31][CH3:32])=[O:30])[CH2:20]1.C(OC)(C)(C)C>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([CH2:15][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH:21]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[C:28]=4[C:29]([O:31][CH3:32])=[O:30])[CH2:20]3)[N:14]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 21980299Methyl 2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoateHCID 224936662-(4-Bromophenyl)4-iodomethyl-5-methyloxazole

Product 1

HCID 22493646Methyl 2-{3-[2-(4-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 50 mg of a 60% sodium hydride suspension and then 408 mg of 2-(4-bromophenyl)-4-iodomethyl-5-methyloxazole were added to a solution of 200 mg of methyl 2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoate in 5 ml of dimethylformamide. After one hour, methyl tert-butyl ether was added, and the mixture was extracted with water. The organic phase was dried over magnesium sulfate, the solvents were removed under reduced pressure and the residue was purified by RP-HPLC. This gave 49 as a light-yellow oil. C27H30BrNO5 (528.45), MS(ESI): 528.2, 530.2 (M+H+).

Workup

  1. extractionthe mixture was extracted with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-35e920e9d42e4192b9e0e2f316c1c05a
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Linked notes

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