Hydrochloric Acid → HCID 44595094, compound

HRID 561515Notes

Reaction equation

HRID 561515 reaction equation
[Cl: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])=[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: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])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392206HCID 58392206, compound

Product 1

HCID 44595094HCID 44595094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6.68 g (17.2 mmol) of the compound from Example 29A in 100 ml of tetrahydrofuran was added dropwise to 60 ml (60 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran under argon in 300 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 flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient). 5.93 g (99% 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 flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)
  7. custom5.93 g (99% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-0e8da810a4f74fa0a9991efbaf06542d
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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