Hydrochloric Acid → HCID 73296093, compound

HRID 2172663Notes

Reaction equation

HRID 2172663 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:12][CH:13]=[CH:14][C:5]=3[C:4](=[O:15])[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]3[CH:26]=[CH:27][C:28]([C:30]([OH:32])=[O:31])=[CH:29][C:22]=3[S:21]1(=[O:34])=[O:33])[CH:8]=[CH:9][CH:10]=2.[OH-:35].[Na+].Cl>C(O)C>[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:12][CH:13]=[CH:14][C:5]=3[C:4](=[O:15])[N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:21]([C:22]1[CH:29]=[C:28]([C:30]([OH:32])=[O:31])[CH:27]=[CH:26][C:23]=1[C:24]([OH:35])=[O:25])(=[O:34])=[O:33])[CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 73296091HCID 73296091, compound

Product 1

HCID 73296093HCID 73296093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 9 (50 mg) and aqueous 1N NaOH (3 mL) was stirred at room temperature for 10 min. To this suspension, ethanol (2 mL) was added until the solution became clear. Stirring was continued for 2 h until starting material was disappeared. The solution was poured into ice-water and acidified with 37% HCl to a pH of 1. The resulted mass was extracted with ethylacetate, the organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under vacuum to get the crude product. The crude residue was recrystallized using EtOAc-Hexane-DCM to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 13.5 (bs, 1H), 9.30 (bs, 1H), 8.58-8.35 (m, 4H), 8.05 (d, J=8.0 Hz, 1H), 7.99-7.86 (m, 2H), 7.65-7.52 (m, 2H), 4.01-3.97 (m, 2H), 3.50-3.40 (m, 2H), 1.52-1.40 (m, 4H). MS (ES−) m/z 495 (M−H)−.

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. extractionThe resulted mass was extracted with ethylacetate
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto get the crude product
  8. customThe crude residue was recrystallized

Sources & evidence

ORD record
ord-f3478112a87f4d1393b2f6487c809e66
Source dataset
uspto-grants-2015_06
Patent number
US09056835B2

Reaction notes

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