Hydrochloric Acid → HCID 58392164, compound

HRID 561523Notes

Reaction equation

HRID 561523 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[C:4]([CH3:27])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[C:4]([CH3:27])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392089HCID 58392089, compound

Product 1

HCID 58392164HCID 58392164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 585 mg (1.52 mmol) of the compound from Example 43A in 15 ml of tetrahydrofuran was added dropwise to 5.3 ml (5.31 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 30 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 15 min and then, while cooling in ice, 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 369 mg (71% of theory) of the title compound.

Workup

  1. temperaturewhile cooling in ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-73f929e3e4d547918af44da34dd5fb78
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…