Sodium Carbonate → HCID 86597949, compound

HRID 854675Notes

Reaction equation

[CH3:1][CH:2]([CH3:35])[C@H:3]([NH:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[O:25][C:26]=2[CH3:27])[CH2:15]1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:36](=[O:39])([O-])[O-:37].[Na+].[Na+]>C(Cl)Cl>[CH3:21][O:20][C:16]1[CH:17]=[CH:18][C:19]([O:37][C:36]([N:11]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][CH2:17][C@@H:16]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=4)[O:25][C:26]=3[CH3:27])[CH2:15]2)[C@@H:3]([CH:2]([CH3:35])[CH3:1])[C:4]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:5])=[O:39])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

130 mg of tert-butyl (S)-3-methyl-2-{2-[cis-3-(5-methyl-2-m-tolyloxazol-4-yl-methoxy)cyclohexyl]ethylamino}butyrate are dissolved in 1 ml of methylene chloride, 2 ml of a sat. sodium carbonate solution are added and the mixture is cooled to 0° C., an excess of the acid chloride is then added and the mixture is stirred at RT for 1 h. The entire reaction solution is applied to a kieselguhr cartridge and the cartridge is washed with 20 ml of methylene chloride. The solvent is removed under reduced pressure. This gives 0.1 g of tert-butyl (S)-2-((4-methoxyphenoxycarbonyl)-{2-[cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]ethyl}amino)-3-methylbutyrate.

Workup

washthe cartridge is washed with 20 ml of methylene chloride
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-fe94206b8d18400ab86662f5532e18b1
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259177B2

Reaction notes

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