HCID 18791358, compound → HCID 18791397, compound

HRID 1005604Notes

Reaction equation

HRID 1005604 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:51]=[CH:50][CH:49]=[CH:48][C:14]=1[C:15]([NH:17][C:18]1[CH:45]=[CH:44][C:21]([C:22]([N:24]([CH3:43])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](OCC)=[O:39])=[O:23])=[CH:20][C:19]=1[O:46][CH3:47])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:51]=[CH:50][CH:49]=[CH:48][C:14]=1[C:15]([NH:17][C:18]1[CH:45]=[CH:44][C:21]([C:22]([N:24]([CH3:43])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])=[O:23])=[CH:20][C:19]=1[O:46][CH3:47])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18791358HCID 18791358, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18791397HCID 18791397, compoundYield 121.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-(5-ethoxycarbonylpent-1-yl)oxy-4-methylphenyl]benzamide (400 mg) in tetrahydrofuran (5 ml) was added lithium aluminum hydride (12 mg) at -23° C. and the mixture was stirred at 0° C. for 3 hours. The reaction was quenched with slow addition of 0.5N hydrochloric acid (15 ml) and the solution was stirred at ambient temperature for 20 minutes. The solution was extracted with chloroform (15 ml×3) and the organic layer was washed with aqueous saturated sodium bicarbonate solution and brine. The solution was dried over magnesium sulfate and the solvent was removed under reduced pressure to give 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-(6-hydroxyhex-1-yl)oxy-4-methylphenyl]benzamide (456 mg).

Workup

  1. customThe reaction was quenched with slow addition of 0.5N hydrochloric acid (15 ml)
  2. stirringthe solution was stirred at ambient temperature for 20 minutes
  3. extractionThe solution was extracted with chloroform (15 ml×3)
  4. washthe organic layer was washed with aqueous saturated sodium bicarbonate solution and brine
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4aa6d23700774a08a105212c04ac9234
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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