Hydrochloric Acid → HCID 21884816, compound

HRID 1662992Notes

Reaction equation

HRID 1662992 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH:31]=[CH2:32])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)=[CH:10][CH:9]=1)C.O.[OH-].[Li+].O.Cl>C1COCC1.CO>[CH2:29]([O:28][C:25]1[CH:24]=[CH:23][C:22]([S:19]([N:6]([CH2:5][C:4]([OH:33])=[O:3])[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)=[CH:10][CH:9]=2)(=[O:21])=[O:20])=[CH:27][CH:26]=1)[CH2:30][CH:31]=[CH2:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67434957HCID 67434957, compound

Product 1

HCID 21884816HCID 21884816, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.61 g (7.67 mmol) of [(4-but-3-enyloxy-benzenesulfonyl)-(4-[1,2,4]triazol-1-yl-benzyl)-amino]-acetic acid ethyl ester in 38 ml of THF and 38 ml of MeOH, 0.966 g (23 mmol) of lithium hydroxide monohydrate and 4 ml of H2O are added at 0-5° C. After being stirred for 3.5 h, the reaction mixture is acidified with 2 N aqueous hydrochloride at 0-5° C. and concentrated under reduced pressure to give [(4-but-3-enyloxy-benzenesulfonyl)-(4-[1,2,4]triazol-1-yl-benzyl)-amino]-acetic acid as a colorless powder. To a solution of 3.76 g of the above prepared acid and 1.87 g (13.81 mmol) of 1-hydroxybenztriazole (HOBT) in 35 ml of DMF, 1.61 g (15.34 mmol) of O-(1-methyoxy-1-methyl-ethyl)-hydroxylamine and 1.91 g (12.275 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide are added successively at 0° C. After being stirred for 3.5 h at r.t., the reaction mixture is poured into ice water and the mixture is extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: n-Hexane:AcOEt=1:3˜1:4) to give the title compound. 1H-NMR (400 MHz, CDCl3): 1.34 (s, 6H), 2.55-2.65 (m, 2H), 3.29 (s, 3H), 3.73 (s, 2H), 4.09 (t, J=6.60 Hz, 2H), 4.44 (s, 2H), 5.10-5.25 (m, 2H), 5.85-5.95 (m, 1H), 7.01 (d, 2H, J=8.52 Hz), 7.44 (d, 2H, J=8.0 Hz), 7.64 (d, 2H, J=8.52 Hz), 7.81 (d, 2H, J=8.0 Hz), 8.10 (s, 1H), 8.54 (s, 1H), 8.62 (brs, 1H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bdcbe0ff22004d0cb0de231c7460be06
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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