Sodium borohydride → HCID 18791562, compound

HRID 1005601Notes

Reaction equation

HRID 1005601 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:55]=[CH:54][CH:53]=[CH:52][C:14]=1[C:15]([NH:17][C:18]1[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[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]([N:40]2[CH2:45][CH2:44][C:43](=[O:46])[CH2:42][CH2:41]2)=[O:39])=[O:23])=[CH:20][C:19]=1[O:50][CH3:51])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:55]=[CH:54][CH:53]=[CH:52][C:14]=1[C:15]([NH:17][C:18]1[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[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]([N:40]2[CH2:41][CH2:42][CH:43]([OH:46])[CH2:44][CH2:45]2)=[O:39])=[O:23])=[CH:20][C:19]=1[O:50][CH3:51])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18791297HCID 18791297, compound

Product 1

HCID 18791562HCID 18791562, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-oxopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (192 mg) in methanol (5 ml) was added sodium borohydride (19 mg) at ambient temperature and the mixture was stirred at the same temperate for 1 hour. The reaction was quenched with 0.5N hydrochloric acid (10 ml) and the mixture was extracted with chloroform (15 ml×3). The organic layer was washed with aqueous sodium hydrogen carbonate and brine, and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo to give 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-hydroxypiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (199 mg).

Workup

  1. customThe reaction was quenched with 0.5N hydrochloric acid (10 ml)
  2. extractionthe mixture was extracted with chloroform (15 ml×3)
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate and brine
  4. dry with materialthe solution was dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ff86be55fead4fc1bbe189cb11cfceb7
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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