Lithium Hydroxide → HCID 11542285, compound

HRID 2265253Notes

Reaction equation

HRID 2265253 reaction equation
C[O:2][C:3](=[O:43])[C@@H:4]([NH:20][C:21](=[O:42])[C:22]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=1[NH:29][S:30]([C:33]1[C:38]2=[N:39][S:40][N:41]=[C:37]2[CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[Li+].[OH-]>Cl.C1COCC1>[N:41]1[S:40][N:39]=[C:38]2[C:33]([S:30]([NH:29][C:23]3[CH:24]=[C:25]([I:28])[CH:26]=[CH:27][C:22]=3[C:21]([NH:20][C@@H:4]([CH:5]([C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=3)[C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[C:3]([OH:43])=[O:2])=[O:42])(=[O:31])=[O:32])=[CH:34][CH:35]=[CH:36][C:37]=12

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68768802HCID 68768802, compound

Product 1

HCID 11542285HCID 11542285, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoylamino]-3,3-bis-(4-chloro-phenyl)-propionic acid methyl ester (49 mg, 0.064 mmol), THF (2 mL), and LiOH (1 M in water, 1 mL) was stirred vigorously overnight at rt. The mixture was acidified with conc. HCl (4 drops), diluted with THF to 3.5 mL, and purified by preparative reverse phase HPLC to provide 37 mg (77%) of the acid as a white solid. HPLC: RT=10.62 min. MS (ESI−): mass calcd. for C28H19Cl2IN4O5S2, 753.42; m/z found, 751/753 [M−H]−. 1H NMR (500 MHz, MeOD): 8.32 (dd, J=7.1, 0.9, 1H), 8.24 (dd, J=8.8, 0.8, 1H), 7.95 (d, J=1.5, 1H), 7.76 (dd, J=8.8, 7.1, 1H), 7.38-7.21 (m, 9H), 6.72 (d, J=8.3, 1H), 5.37 (d, J=11.5, 1H), 4.50 (d, J=11.5, 1H).

Workup

  1. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-f28fee46e3434dd2a1a7d94d4aacf6da
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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