Hydrochloric Acid → HCID 10141284, compound

HRID 1169288Notes

Reaction equation

HRID 1169288 reaction equation
[CH2:1]([N:8]([C:33](=[O:39])[C:34]([O:36]CC)=[O:35])[CH2:9][CH:10]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[CH2:1]([N:8]([C:33](=[O:39])[C:34]([OH:36])=[O:35])[CH2:9][CH:10]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 91297772HCID 91297772, compound

Product 1

HCID 10141284HCID 10141284, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 16C (50.0 mg, 0.096 mmol) in ethanol (2 mL) at room temperature was treated with 2M NaOH (0.2 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 492 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ8.04-7.83 (m, 2H), 7.67-7.00 (m, 14H), 4.54-4.33 (m, 1H), 3.93-3.62 (m, 1H), 3.00-2.70 (m, 1H), 1.83-0.67 (m, 11H).

Workup

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

Sources & evidence

ORD record
ord-8c6b7fb55d9e46718bf11b4d66661205
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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