Hydrochloric Acid → HCID 9913602, compound

HRID 1662993Notes

Reaction equation

HRID 1662993 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)=[CH:29][CH:28]=2)[CH2:16][C:17]([NH:19][O:20]C(OC)(C)C)=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].Cl.C([O-])(O)=O.[Na+]>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)=[CH:31][CH:32]=2)[CH2:16][C:17]([NH:19][OH:20])=[O:18])(=[O:13])=[O:14])=[CH:10][CH:11]=1)[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21884784HCID 21884784, compound

Product 1

HCID 9913602HCID 9913602, compound

Procedure

To a solution of 0.39 g (0.74 mmol) of 2-[(4-but-3-enyloxy-benzenesulfonyl)-(4-imidazol-1-yl-benzyl)-amino]-N-(1-methoxy-1-methyl-ethoxy)-acetamide (stage 80.4), 2.46 ml of 6 N aqueous hydrochloride is added at r.t. After being stirred for 15 min, the reaction mixture is neutralized with sat. NaHCO3 and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to give 2-[(4-but-3-enyloxy-benzenesulfonyl)-(4-imidazol-1-yl-benzyl)-amino]-N-hydroxy-acetamide as a colorless powder. To a solution of 0.17 g (0.37 mmol) of the above prepared hydroxy acetamide in 3 ml of dioxane, 0.447 ml of 1 N aqueous hydrochloride is added and stirred for 10 min. The reaction mixture is concentrated under reduced pressure and dried in vacuo to give their title compound. 1H-NMR (400 MHz, DMSO-d6): 2.40-2.50 (m, 2H), 3.61 (s, 2H), 4.07 (t, 2H, J=6.52 Hz), 4.37 (s, 2H), 5.00-5.15 (m, 2H), 5.75-5.90 (m, 1H), 7.04 (d, 2H, J=8.56 Hz), 7.48 (d, 2H, J=8.56 Hz), 7.65-7.75 (m, 5H), 7.81 (s, 1H), 8.19 (s, 1H), 9.57 (s, 1H), 10.54 (brs, 1H).

Workup

  1. extractionextracted with AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64caf257a1594a3e8520fb60fbd66187
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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