Hydrochloric Acid → HCID 58392477, compound

HRID 561526Notes

Reaction equation

HRID 561526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:9][CH2:10][C:11](OCC)=[O:12])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392214HCID 58392214, compound

Product 1

HCID 58392477HCID 58392477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 420 mg (1.05 mmol) of the compound from Example 46A in 10 ml of tetrahydrofuran was added dropwise to 3.7 ml (3.7 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran under argon in 20 ml of tetrahydrofuran at RT. 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 residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). 243 mg (65% of theory) of the target compound were obtained.

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 residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
  7. custom243 mg (65% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-5dc3bd1470ab47f197e8dcedf3075e9b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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