Ammonia → HCID 67596078, compound

HRID 1603015Notes

Reaction equation

[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:23](=[O:27])(=O)(O)[OH:24].ClS(O)(=O)=O.[NH3:33].[CH2:34](O)[CH3:35]>>[NH2:33][S:23]([C:15]1[CH:14]=[CH:13][C:12]([C:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][O:9][C:10]=2[CH:18]([CH3:22])[C:19]([O:21][CH2:34][CH3:35])=[O:20])=[CH:17][CH:16]=1)(=[O:27])=[O:24]

Participants

Reactant 5

HCID 222Ammonia

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 24638Chlorosulfonic acid

HCID 19608709HCID 19608709, compound

Product 1

HCID 67596078HCID 67596078, compoundYield 60%

Procedure

A solution of [3,4-diphenylisoxazol-5-yl]propanoic acid was treated with ethanol in the presence of a catalytic amount of sulfuric acid to prepare the corresponding ethyl ester which was immediately treated with chlorosulfonic acid followed by ammonia according to the procedure from Example 2, Step 4. The crude sulfonamide was purified by flash chromatography eluting with ethyl acetate/hexane (10-50% ethyl acetate) to yield, upon concentration of the appropriate fractions, ethyl [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]propanoate as a glassy solid (248 mg, 60%): Mass spectrum: MH+=401. 1H NMR (CDCl3 /300 MHz) δ 7.93 (d, J=8.46 Hz, 2H); 7.41-7.30 (m, 7H), 4.84 (s, 2H), 4.14 (q, J=7.04 Hz, 2H), 3.12 (t, J=7.45 Hz, 2H), 2.81 (t, J=7.45 Hz, 2H), 1.25 (t, J=7.04 Hz, 3H). This material was used directly in the next step without further purification.

Workup

customThe crude sulfonamide was purified by flash chromatography
washeluting with ethyl acetate/hexane (10-50% ethyl acetate)

Sources & evidence

ORD record: ord-e9547fef3e7c471dadf51f06b18a5b47
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05985902

Reaction notes

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