Hydrochloric Acid → HCID 66757799, compound

HRID 242554Notes

Reaction equation

HRID 242554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:46])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][C:24]([C:28](=[O:30])[NH2:29])=[CH:25][CH:26]=4)[O:21][C:20]4[CH:31]=[CH:32][CH:33]=[C:34]([N:35]5[CH2:40][CH2:39][CH:38]([C:41]([O:43]CC)=[O:42])[CH2:37][CH2:36]5)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:46])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][C:24]([C:28](=[O:30])[NH2:29])=[CH:25][CH:26]=4)[O:21][C:20]4[CH:31]=[CH:32][CH:33]=[C:34]([N:35]5[CH2:40][CH2:39][CH:38]([C:41]([OH:43])=[O:42])[CH2:37][CH2:36]5)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66758500HCID 66758500, compound

Product 1

HCID 66757799HCID 66757799, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound of Example 420 (91 mg, 0.14 mmol) in MeOH (5 mL) was treated with a 0.4 M solution of lithium hydroxide (5 mL, 2 mmol) and stirred for 3 hours. After addition of 5 mL of 0.4 N HCl, the solvent was removed under reduced pressure to give the crude product. The residue was purified using silica gel chromatography eluting with a dichloromethane:methanol gradient (0 to 50% MeOH over 1 hour) to give the title compound (48 mg).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto give the crude product
  3. customThe residue was purified
  4. washeluting with a dichloromethane

Sources & evidence

ORD record
ord-e7c4c3b07e41419d8f42a46ce4d4cf7b
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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