Lithium Hydroxide → [7-(Methanesulfonyl-methyl-amino)-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl]-acetic acid

HRID 2374376Notes

Reaction equation

HRID 2374376 reaction equation
[OH-].[Li+].C(OC([N:10]1[C:15]2[CH:16]=[CH:17][C:18]([N:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH3:21])=[CH:19][C:14]=2[S:13](=[O:27])(=[O:26])[CH:12]=[C:11]1[CH2:28][C:29]([O:31]C)=[O:30])=O)(C)(C)C>CO>[CH3:25][S:22]([N:20]([CH3:21])[C:18]1[CH:17]=[CH:16][C:15]2[NH:10][C:11]([CH2:28][C:29]([OH:31])=[O:30])=[CH:12][S:13](=[O:26])(=[O:27])[C:14]=2[CH:19]=1)(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 598535787-(methanesulfonyl-methyl-amino)-3-methoxycarbonylmethyl-1,1-dioxo-1H-1lambda6-benzo[1,4]thiazine-4-carboxylic acid tert-butyl ester

Product 1

HCID 59853596[7-(Methanesulfonyl-methyl-amino)-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl]-acetic acidYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A 2.0 M aqueous solution of lithium hydroxide (7.0 mL, 14.0 mmol) was added to a solution of 7-(methanesulfonyl-methyl-amino)-3-methoxycarbonylmethyl-1,1-dioxo-1H-1λ6-benzo[1,4]thiazine-4-carboxylic acid tert-butyl ester (Example 7d, 1.29 g, 2.80 mmol) in methanol at 25° C. The reaction mixture was stirred at 25° C. for 5 h, and then was partitioned between 0.5 M aqueous hydrochloric acid solution (150 mL) and ethyl acetate (2×150 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Trituration of the residue with a 5:1 mixture of diethyl ether and acetonitrile afforded the desired product, [7-(methanesulfonyl-methyl-amino)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl]-acetic acid (0.286 g, 0.83 mmol, 30% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ: 2.96 (3H, s), 3.26 (3H, s), 3.48 (2H, s), 6.03 (1H, s), 7.29 (1H, d, J=8.6 Hz), 7.58 (1H, dd, J1=2.3 Hz, J2=9.5 Hz), 7.79 (1H, d, J=2.3 Hz), 10.80 (1H, s), 12.79 (1H, s).

Workup

  1. customwas partitioned between 0.5 M aqueous hydrochloric acid solution (150 mL) and ethyl acetate (2×150 mL)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionTrituration of the residue with a 5:1 mixture of diethyl ether and acetonitrile

Sources & evidence

ORD record
ord-8e844291ecb84666b398992a2bb5315c
Source dataset
uspto-grants-2008_12
Patent number
US07462611B2

Reaction notes

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