Hydrochloric Acid → HCID 70242089, compound

HRID 1531798Notes

Reaction equation

HRID 1531798 reaction equation
[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]([CH2:26][C:27]([O:29]C)=[O:28])[CH2:23]3)=[CH:18][CH:17]=2)[C@@H:10]([CH3:39])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1.CO>[CH2:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:23]3)=[CH:18][CH:17]=2)[C@@H:10]([CH3:39])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90897044HCID 90897044, compound

Product 1

HCID 70242089HCID 70242089, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound of Example 104 (0.85 g) in dioxan (20 ml) and methanol (10 ml) was added an aqueous solution of sodium hydroxide (2N, 5 ml). After 16 hours, the pH of the reaction was adjusted to pH5 using 1N aqueous hydrochloric acid solution and the solvent removed under reduced pressure. The crude product was purified on silica gel, eluting with a solvent gradient of 90:10:2 to 80:20:3 dichloromethane: methanol:ammonia solution. The fractions containing the product were pooled and the solvent removed under reduced pressure. The residue was taken up in a mixture of water and 1 drop of aqueous ammonium hydroxide solution and freeze-dried to give the title compound (0.65 g, 65%).

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe crude product was purified on silica gel
  3. washeluting with a solvent gradient of 90:10:2 to 80:20:3 dichloromethane
  4. additionThe fractions containing the product
  5. customthe solvent removed under reduced pressure
  6. additionThe residue was taken up in a mixture of water and 1 drop of aqueous ammonium hydroxide solution
  7. customfreeze-dried

Sources & evidence

ORD record
ord-914d66e4643b4f82ae1422a698047269
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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