Hydrochloric Acid → HCID 58392440, compound

HRID 561525Notes

Reaction equation

HRID 561525 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:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:14][C:15](OCC)=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.C(OCC)(=O)C>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:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 58392316HCID 58392316, compound

Product 1

HCID 58392440HCID 58392440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 600 mg (1.49 mmol) of the compound from Example 45A in 15 ml of tetrahydrofuran was added dropwise to 5.2 ml (5.2 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 30 ml of tetrahydrofuran at RT under argon. Stirring at RT for 15 min was followed by addition, while cooling in ice, of 1N hydrochloric acid, extraction with ethyl acetate, drying of the organic phase over magnesium sulfate, filtration and concentration. 486 mg (90% of theory) of the title compound were obtained.

Workup

  1. additionwas followed by addition
  2. dry with materialdrying of the organic phase over magnesium sulfate, filtration and concentration

Sources & evidence

ORD record
ord-a0bbaeb05d4141fa8a37789d648ab5bb
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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