Hydrochloric Acid → HCID 10272572, compound

HRID 1169284Notes

Reaction equation

HRID 1169284 reaction equation
[CH:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:18]=2)[O:8][NH:9][C:10](=[O:16])[C:11]([O:13]CC)=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:18]=2)[O:8][NH:9][C:10](=[O:16])[C:11]([OH:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90737469HCID 90737469, compound

Product 1

HCID 10272572HCID 10272572, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 4A (70 mg, 0.162 mmol) in ethanol (2 mL) at room temperature was treated with 2M NaOH (1 mL), stirred for 2 hours, adjusted to pH 1 with 1M HCl, and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/z 405 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ11.96 (br s, 1H), 8.49 (d, 1H), 8.23-8.17 (m, 3H), 8.06 (d, 1H), 8.02 (d, J=8.2 Hz, 1H), 7.80 (dt, 1H), 7.61 (dt, 1H), 7.53 (t, 1H), 7.43 (d, 1H), 4.82 (d, 1H), 2.08 (m, 1H), 1.82-1.70 (m, 2H), 1.60 (m, 2H), 1.48-1.10 (m, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-984dd97961eb44448e2fcfc42d72e833
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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