HCID 19844116, compound → HCID 19844111, compound

HRID 2352312Notes

Reaction equation

HRID 2352312 reaction equation
O.[ClH:2].[CH3:3][N:4]([CH3:29])[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)(=[O:18])=[O:17])[CH:14]=2)[NH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[ClH:2].[CH3:29][N:4]([CH3:3])[CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)(=[O:17])=[O:18])[CH:14]=2)[NH:9][CH:8]=1

Participants

4

Reactant 2

HCID 19844116HCID 19844116, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19844111HCID 19844111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of the product of stage (i) (0.9 g) in tetrahydrofuran (15 ml) was added dropwise, under nitrogen, to a stirred suspension of lithium aluminium hydride (0.5 g) in tetrahydrofuran (10 ml) and the resulting mixture heated at reflux for 16 h. The mixture was cooled and excess reducing agent decomposed by cautious addition of 10% aqueous tetrahydrofuran. The resulting mixture was partitioned betweeen sodium carbonate (2 N, 75 ml) and ethyl acetate (2×50 ml) and the combined extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound free base as an oil. The oil was dissolved in absolute ethanol (10 ml) acidified with ethereal hydrogen chloride and the salt precipitated by addition of excess dry ether (150 ml). the salt was filtered off, and dried in vacuo to give the title compound as a solid (0.42 g), m.p. 119°-121°.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 16 h
  3. temperatureThe mixture was cooled
  4. customThe resulting mixture was partitioned betweeen sodium carbonate (2 N, 75 ml) and ethyl acetate (2×50 ml)
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f96700c268364aa9ab66045e866a845c
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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