Hydrochloric Acid → (S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid

HRID 2265277Notes

Reaction equation

HRID 2265277 reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:14][C:15](=[O:36])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[NH:23][S:24]([C:27]1[C:32]2=[N:33][S:34][N:35]=[C:31]2[CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1.C1COCC1.[Li+].[OH-].Cl>O>[N:35]1[S:34][N:33]=[C:32]2[C:27]([S:24]([NH:23][C:17]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=3[C:15]([NH:14][C@@H:4]([CH2:5][C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=3)[C:3]([OH:37])=[O:2])=[O:36])(=[O:25])=[O:26])=[CH:28][CH:29]=[CH:30][C:31]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68771712(S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl ester

Product 1

HCID 45255234(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl ester (0.81 mmol), THF (10 mL), and LiOH (2 M in water, 5 mL) was stirred vigorously overnight at rt. The mixture was poured into water, acidified to pH 1 with conc. HCl, and extracted with EtOAc (4×). The combined organic layers were dried (Na2SO4) and concentrated to provide the desired acid as a tan solid. The acid was purified by preparative reverse phase HPLC to provide 0.44 g (94%, 2 steps) of the acid as a white solid. HPLC: RT=10.08 min. MS (ESI−): mass calcd. for C22H15Cl3N4S5O2, 583.95; m/z found, 583 [M−H]−. 1H NMR (400 MHz, CD3OD): 8.34 (dd, J=7.0, 1.0, 1H), 8.25 (dd, J=8.8, 1.0, 1H), 7.77 (dd, J=8.8, 7.0, 1H), 7.66 (d, J=2.0, 1H), 7.45-7.37 (m, 3H), 7.18 (dd, J=8.2, 2.0, 1H), 6.99 (dd, J=8.5, 2.1, 1H), 4.75 (dd, J=9.3, 5.2, 1H), 3.28 (dd, J=14.0, 5.1, 1H), 3.03 (dd, J=14.0, 9.4, 1H).

Workup

  1. extractionextracted with EtOAc (4×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9821d56d43a941758c27f041c4bfbbb7
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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