Hydrochloric Acid → HCID 21480498, compound

HRID 1490045Notes

Reaction equation

HRID 1490045 reaction equation
C(OC([O:6][CH2:7][CH2:8][N:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][C:12]2[CH:20]=[CH:21][S:22][C:11]=2[S:10]1(=[O:24])=[O:23])C)C.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].Cl>CCOCC.CC(C)=O>[OH:6][CH2:7][CH2:8][N:9]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]2[CH:20]=[CH:21][S:22][C:11]=2[S:10]1(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 21480493HCID 21480493, compound

Product 1

HCID 21480498HCID 21480498, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product from Step C (8.77 g, 23.4 mmol) in anhydrous ether (100 mL) at 0° C. was added diisobutylaluminium hydride (1M solution in hexanes, 70.2 mmol). The reaction mixture was stirred for 1 h, a solution of potassium sodium tartrate (28.2 g in 100 mL water) was added, and the resulting mixture stirred for 2 h. The aqueous layer was separated and extracted with ethyl acetate (2×100 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to give an oil which was dissolved in acetone (100 mL) and treated with 100 mL of 2 N HCl for 4 h. The acetone was evaporated and the remaining aqueous mixture was extracted with ethyl acetate (2×100 mL) The combined extracts was dried and evaporated to give a solid (4.82 g, 79%); Recrystallization from EtOAc/Hex gave a crystalline solid: mp 81°-83° C.

Workup

  1. stirringthe resulting mixture stirred for 2 h
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil which
  8. customThe acetone was evaporated
  9. extractionthe remaining aqueous mixture was extracted with ethyl acetate (2×100 mL) The combined extracts
  10. customwas dried
  11. customevaporated

Sources & evidence

ORD record
ord-e9a11fac7ad44c559c45baf8bd73d9e2
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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