Sodium hydride → Ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)-cyclohexyloxy]ethoxy}benzoate

HRID 553570

Reaction equation

[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([O:35][CH2:36][C:37]3[N:38]=[C:39]([C:43]4[CH:44]=[C:45]([CH3:49])[CH:46]=[CH:47][CH:48]=4)[O:40][C:41]=3[CH3:42])[CH2:30]2)(=O)=O)=CC=1>CN(C=O)C.[Na+].[Cl-].C(OCC)(=O)C>[CH3:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([O:1][CH2:26][CH2:27][O:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([O:35][CH2:36][C:37]3[N:38]=[C:39]([C:43]4[CH:44]=[C:45]([CH3:49])[CH:46]=[CH:47][CH:48]=4)[O:40][C:41]=3[CH3:42])[CH2:30]2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 40 °C

Procedure

90 mg of ethyl 2-hydroxy-6-methylbenzoate are dissolved in 2 ml of dry DMF, and 23 mg of a 60 percent strength sodium hydride suspension are added. After 30 min at room temperature, 100 mg of ((1R,3S)-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethyl toluene-4-sulfonate in 2 ml of DMF are added. The mixture is stirred at 40° C. until the reaction has gone to completion (monitored by LC-MS). After cooling, the mixture is diluted with sat. NaCl solution and ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. This gives ethyl (1R,3S)-2-methyl-6-{2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]ethoxy}benzoate as a yellowish oil. C30H37NO6 (507.63), MS (ESI): 508 (M+H+).

Workup

temperatureAfter cooling
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-f06fe5ff6da749bab460989d306cfb63
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048901B2

Linked notes

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