Methyl 3-[4-(chlorosulfonyl)phenyl]propanoate → HCID 11519234, compound

HRID 869340Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]([O:15]C)=[N:13][C:12]2[C:7]1=[N:8][C:9]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N:10][C:11]=2[NH2:17].Cl[S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>C(N(CC)CC)C>[NH2:17][C:11]1[N:10]=[C:9]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:8]=[C:7]2[C:12]=1[NH:13][C:14](=[O:15])[N:6]2[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:24]([C:27]1[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:32]=1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

The compound obtained in Example 2-8 step (ii) (308 mg), methyl 3-[4-(chlorosulfonyl)phenyl]propanoate (263 mg) and triethylamine (0.284 ml) were mixed under stirring at 60° C. for 1 hour, and then cooled. After concentration under reduced pressure, the residue was purified by RPHPLC. The resulting white substance was dissolved in methanol, and 4M hydrochloric acid-dioxane was added thereto. The mixture was stirred at room temperature overnight and then concentrated under reduced pressure to give the titled compound as a white solid. Yield: 124 mg (24%); mp 150-152° C., MS APCI+ve 521 (M+H).

Workup

temperaturecooled
concentrationAfter concentration under reduced pressure
customthe residue was purified by RPHPLC
dissolutionThe resulting white substance was dissolved in methanol
addition4M hydrochloric acid-dioxane was added
stirringThe mixture was stirred at room temperature overnight
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0d2c9c57e44446cf9f97912d657c389c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969362B2

Reaction notes

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