Hydrochloric Acid → HCID 21884816, compound

HRID 722464Notes

Reaction equation

HRID 722464 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+].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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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-benzensulfonyl)-(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 lithum hydroxide monohydrate and 4 ml of H 20 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-benzensulfonyl)-(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-aa4854698244431b88482a17e2355a65
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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