Hydrochloric Acid → 3-(2-Dipropylcarbamoylmethoxycarbonyl-ethylsulfamoyl)-benzoic acid

HRID 2170103Notes

Reaction equation

FC(F)(F)C(O)=O.[CH2:8]([N:11]([CH2:21][CH2:22][CH3:23])[C:12]([CH2:14][O:15][C:16](=[O:20])[CH2:17][CH2:18][NH2:19])=[O:13])[CH2:9][CH3:10].Cl[S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26].O.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:21]([N:11]([CH2:8][CH2:9][CH3:10])[C:12]([CH2:14][O:15][C:16]([CH2:17][CH2:18][NH:19][S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26])=[O:20])=[O:13])[CH2:22][CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-amino-propionic acid dipropylcarbamoylmethyl ester (step 2) (20.1 g, 75 mmol) in DCM (240 ml) at 0° C. under N2 was added DMAP (0.46 g, 3.76 mmol) followed by TEA (38.8 ml, 278 mmol). The reaction mixture was treated with a solution of 3-chlorosulfonylbenzoic acid (16.6 g, 75 mmol) in DCM (200 ml). The mixture was allowed to stir at 0° C. for 1 h and then warmed up to RT for 1 h. Water (200 ml) was added and the pH adjusted with 1N HCl (100 ml). The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification by C18 reverse phase chromatography, eluting with MeCN/water (1% HCl) afforded the title product; LC-MS Rt 1.01 mins; 415.2 [M+H]+, Method 2minLC_v003.

Workup

temperaturewarmed up to RT for 1 h
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification by C18 reverse phase chromatography
washeluting with MeCN/water (1% HCl)

Sources & evidence

ORD record: ord-8f786711be854190a216f0b30a15cfbd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050339B2

Reaction notes

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