Hydrochloric Acid → HCID 22882588, compound

HRID 863268Notes

Reaction equation

HRID 863268 reaction equation
Cl.[CH:2]([Si:5]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[O:6][CH2:7][CH2:8][C@@H:9]([CH3:24])[CH2:10][C@@H:11]1[N:16]=C(OC)[C@@H](C(C)C)N=[C:12]1[O:22][CH3:23])([CH3:4])[CH3:3].[OH-:31].[Na+]>O1CCCC1>[NH2:16][C@@H:11]([CH2:10][C@H:9]([CH3:24])[CH2:8][CH2:7][O:6][Si:5]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:2]([CH3:4])[CH3:3])[C:12]([O:22][CH3:23])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22882399HCID 22882399, compound

Product 1

HCID 22882588HCID 22882588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 ml of 0.5N hydrochloric acid are added to a solution of 10.0 g of 3,6-dihydro-3(S)-[4-triisoproylsilyloxy-2(S)-methylbutyl]-6(R)-isopropyl-2,5-dimethoxypyrazine in 100 ml of tetrahydrofuran and the mixture is stirred at room temperature for 40 min. The reaction mixture is brought to pH 9 by addition of 1N sodium hydroxide solution and then extracted with methylene chloride. The combined organic phase is filtered through cotton wool and concentrated. The crude product is purified by FC over 900 g of silica gel with a 500:10:1 mixture of methylene chloride, methanol and 25% ammonia solution. In addition to the re-isolated starting material, this gives the title compound: Rf (methylene chloride-methanol-concentrated ammonia: (140:10:1))=0.34.

Workup

  1. extractionextracted with methylene chloride
  2. filtrationThe combined organic phase is filtered through cotton wool
  3. concentrationconcentrated
  4. customThe crude product is purified by FC over 900 g of silica gel with a 500:10:1 mixture of methylene chloride, methanol and 25% ammonia solution
  5. additionIn addition to the re-isolated

Sources & evidence

ORD record
ord-e6d028241bb04a0593549facee008329
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…