Hydrochloric Acid → HCID 44595093, compound

HRID 561514Notes

Reaction equation

HRID 561514 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)[CH2:14][C:15](OCC)=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]([C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=1)[CH2:14][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392151HCID 58392151, compound

Product 1

HCID 44595093HCID 44595093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 215 mg (0.51 mmol) of the compound from Example 25A was added dropwise to 1.8 ml (1.80 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran under argon in 10 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. Purification by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient) resulted in 169 mg (87% 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. customPurification by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient)

Sources & evidence

ORD record
ord-c966cf0b7a534ed1955d50ca8259bfcb
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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