Hydrochloric Acid → HCID 69688802, compound

HRID 1840620Notes

Reaction equation

HRID 1840620 reaction equation
[OH-].[Li+].[CH3:3][C:4]1([CH3:52])[C:8](=[O:9])[N:7]([C@@H:10]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:11]([NH:13][CH:14]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][C:16]([O:18]CC)=[O:17])=[O:12])[C:6](=[O:31])[N:5]1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH3:49])=[O:41])=[C:35]([O:50][CH3:51])[CH:34]=1.[ClH:53]>CO>[ClH:53].[CH3:3][C:4]1([CH3:52])[C:8](=[O:9])[N:7]([C@@H:10]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:11]([NH:13][CH:14]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][C:16]([OH:18])=[O:17])=[O:12])[C:6](=[O:31])[N:5]1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[CH3:49])=[O:41])=[C:35]([O:50][CH3:51])[CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 12044592HCID 12044592, compound

Product 1

HCID 69688802HCID 69688802, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.82 mL (0.82 mmol) of a 1 M aqueous lithium hydroxide solution was added to a solution of 141 mg (0.206 mmol) of the compound of Example 9 in 7.25 mL of methanol and the reaction mixture was allowed to stand overnight at room temperature. The methanol was then removed in vacuo, the residue was adjusted to pH 2 using 1N hydrochloric acid and the mixture was concentrated in vacuo. The residue was chromatographed over silica gel using dichloromethane/methanol/glacial acetic acid/water (95/5/0.5/0.5). After concentrating the product fractions, the residue was treated with 1.11 equivalents of 1N hydrochloric acid and freeze dried. Yield: 120 mg (89%).

Workup

  1. customThe methanol was then removed in vacuo
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was chromatographed over silica gel
  4. concentrationAfter concentrating the product fractions
  5. customdried

Sources & evidence

ORD record
ord-6e99ae03685b46bbb5331dfff92a15b5
Source dataset
uspto-grants-2004_01
Patent number
US06680333B2

Reaction notes

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