Lithium Hydroxide → HCID 42633276, compound

HRID 1009023Notes

Reaction equation

C([O:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([S:13]([NH:16][C:17](=[O:30])[NH:18][C:19]2[S:20][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[N:22]=3)(=[O:15])=[O:14])=[CH:10][C:11]=1[CH3:12])(=O)C.[Li+].[OH-]>>[OH:4][CH2:5][CH2:6][C:7]1[S:8][C:9]([S:13]([NH:16][C:17](=[O:30])[NH:18][C:19]2[S:20][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]([O:28][CH3:29])[N:22]=3)(=[O:15])=[O:14])=[CH:10][C:11]=1[CH3:12]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 42633092HCID 42633092, compound

Product 1

HCID 42633276HCID 42633276, compound

Procedure

2-[5-({[(5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)carbamoyl]amino}sulfonyl)-3-methyl-2-thienyl]ethyl acetate (235 mg, 0.5 mmol, 1 equiv.) was saponified by addition of 1N LiOH (1 mL, 1 mmol, 2 equiv.) for 60 min. The solution was purified by chromatography on a HPLC 75×30 mm RP18 5 μm column, with A=0.1% HCOOH and B=MeCN and with a gradient of 20% to 70% B in 10 min. The corresponding fractions were lyophilized to give 5-(2-hydroxyethyl)-N-[(5-methoxy[1,3]thiazolo[5,4-b]pyridin-2-yl)carbamoyl]-4-methylthiophene-2-sulfonamide, 47 mg, m/e 427.0 (MH−).

Workup

customThe solution was purified by chromatography on a HPLC 75×30 mm RP18 5 μm column, with A=0.1% HCOOH and B=MeCN and with a gradient of 20% to 70% B in 10 min

Sources & evidence

ORD record: ord-ef264f68f775477184882e7c24a8fd66
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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