Water → HCID 70074050, compound

HRID 1073672Notes

Reaction equation

HRID 1073672 reaction equation
C([O:3][C:4]([CH:6]1[CH2:19][CH2:18][C:17]2[C:8](=[C:9]([NH:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([Cl:20])=[CH:12][CH:11]=3)[CH2:7]1)=[O:5])C.O.[OH-].[Na+]>C(O)C>[OH2:3].[Cl:20][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:21][NH:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[C:8]1[C:17]([CH2:18][CH2:19][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[N:16]2.[Cl:20][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:21][NH:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[C:8]1[C:17]([CH2:18][CH2:19][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[N:16]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15052673HCID 15052673, compound

Product 1

HCID 70074050HCID 70074050, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.0 g (0.0051 mol) of the compound of Example 10, 6.4 ml of water, 6.4 ml of ethanol, and 0.4 g of NaOH is stirred at ambient temperature overnight, then concentrated in vacuo. The residue is dissolved in water and extracted with ethyl acetate. The aqueous phase is acidified using acetic acid and extracted with methylene chloride. The organic extracts are dried over Na2SO4, and concentrated in vacuo. The resulting powder is triturated with petroleum ether to give 42 mg of the title compound: IR (KBr) 3250 (br), 2940 (br), 2500 (br), 1700 , and 1600 cm-1 ; NMR (DMSO-d6) δ8.18-7.58 (m, 11H), 3.24-2.90 (m, 5H), 2.38-2.22 (m, 1H), and 2.10-1.98 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts are dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting powder is triturated with petroleum ether

Sources & evidence

ORD record
ord-e618ed573c9547a18797c718a169b3a1
Source dataset
uspto-grants-1990_11
Patent number
US04970316

Reaction notes

Loading…