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

HRID 2265169Notes

Reaction equation

HRID 2265169 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]([I: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.O[Li].O.O.Cl>O.C1COCC1>[N:35]1[S:34][N:33]=[C:32]2[C:27]([S:24]([NH:23][C:17]3[CH:18]=[C:19]([I: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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58999935(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl esterHCID 178526967HCID 178526967, compound

Product 1

HCID 11693225(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acidYield 76.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl ester (55 mg, 0.079 mmol) in 2:1 water/THF (3 mL) was added LiOH-2H2O (7 mg, 0.158 mmol). The yellow solution was stirred for 2 h and then 20% aq. HCl (2 mL) was added. The mixture was extracted with EtOAc (3×). The organic layers were combined, dried (MgSO4), and concentrated to provide the desired product as a white solid (41 mg, 76%). HPLC: RT=9.77 min. MS (ESI−): mass calcd. for C22H15Cl2IN4O5S2, 677.3; m/z found, 676 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.22 (s, 1H), 8.33 (d, J=7.0, 1H), 8.12 (d, J=8.8, 1H), 7.98 (d, J=0.8, 1H), 7.70 (dd, J=8.6, 7.3, 1H), 7.33 (d, J=8.2, 1H), 7.22 (d, J=8.2, 1H), 7.02 (dd, J=8.2, 1.6, 1H), 6.93 (d, J=8.3, 1H), 6.73 (d, J=7.3, 1H), 4.99 (q, J=6.3, 1H), 3.31 (dd, J=14.2, 5.7, 1H), 3.20 (dd, J=14.2, 5.7).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fbd7bf7c793447249e05f01a5f0614d2
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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