Ammonium Hydroxide → HCID 66656124, compound

HRID 571801Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH:30]OS([O-])=O.[K+].[NH4+].[OH-]>CO.O.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12](=[O:30])[CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-{2-[4-(2-Chloro-phenoxy)-phenyl]-thiomorpholin-4-yl}-propionic acid tert-butyl ester (0.28 g; 0.65 mmol) in MeOH (10 mL) was added, dropwise, a solution of OXONE® (0.20 g; 0.32 mmol) in water (10 mL), at 0° C. The mixture was stirred for 2 hours at 0° C., and then allowed to warm to room temperature overnight. Subsequently, water, brine, and 25% aqueous NH4OH were added and the mixture extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 98:2) to afford 3-{2-[4-(2-Chloro-phenoxy)-phenyl]-1-oxo-thiomorpholin-4-yl}-propionic acid tert-butyl ester (0.19 g).

Workup

customat 0° C
temperatureto warm to room temperature overnight
extractionthe mixture extracted with EtOAc
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record: ord-7960b30b30114715afa3d9c706477afb
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029371B2

Reaction notes

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