Hydrochloric Acid → HCID 178525543, compound

HRID 220148Notes

Reaction equation

HRID 220148 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C@H:12]3[CH2:17][CH2:16][C@H:15]([CH2:18][C:19]([O:21]CC)=[O:20])[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)=[N:2]1.[OH-].[Li+].Cl>O1CCCC1.O>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C@H:12]3[CH2:13][CH2:14][C@H:15]([CH2:18][C:19]([OH:21])=[O:20])[CH2:16][CH2:17]3)=[CH:10][CH:11]=2)=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178471762HCID 178471762, compound

Product 1

HCID 178525543HCID 178525543, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A scintillation vial was charged with the product from Example 37B (31.3 mg, 0.100 mmol), lithium hydroxide (21 mg, 0.50 mmol) and 10 mL of 4:1 tetrahydrofuran/water and placed in a shaker overnight at room temperature. The reaction was neutralized by the addition of 4 M HCl, and the resultant mixture was concentrated and purified by RP-HPLC to provide the title product. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.07-1.17 (m, 2H), 1.42-1.53 (m, 2H), 1.70-1.88 (m, 5H), 2.14 (d, J=6.75 Hz, 2H), 2.44-2.48 (m, 1H), 6.63 (d, J=2.15 Hz, 1H), 7.26 (d, J=7.97 Hz, 2H), 7.65 (d, J=2.15 Hz, 1H), 7.68 (d, J=7.97 Hz, 2H), 12.46 (br, s, 2H); MS (ESI) m/z 285.0 [M+H]+.

Workup

  1. customplaced in a shaker overnight at room temperature
  2. concentrationthe resultant mixture was concentrated
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-318168b65dbd4c3caa58025e2db4b501
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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