Sodium Hydroxide → HCID 18791670, compound

HRID 1005602Notes

Reaction equation

HRID 1005602 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)[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].C([O-])(=O)C.[NH4+].C([BH3-])#[N:62].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[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][CH:43]([NH2:62])[CH2:42][CH2:41]2)=[O:39])=[O:23])=[CH:20][C:19]=1[O:50][CH3:51])=[O:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18791297HCID 18791297, compound

Product 1

HCID 18791670HCID 18791670, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a mixture 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 (250 mg), ammonium acetate (51 mg) and acetic acid (0.5 ml) in methanol (10 ml) was added sodium cyanoborohydride (21 mg) at 0° C. and the mixture was stirred at ambient temperature for 12 hours. The mixture was poured into ice-cooled 1N aqueous sodium hydroxide solution (15 ml) and the solution was extracted with chloroform (15 ml×3). The organic layer was washed with brine and dried over potassium carbonate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography (SiO2 40 g, 5-15% methanol in chloroform) to give 4-[2-[(3-tert-butoxycarbonylaminoprop-1-yl)oxy]benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-aminopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (91 mg).

Workup

  1. additionThe mixture was poured into ice-
  2. extractionthe solution was extracted with chloroform (15 ml×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over potassium carbonate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (SiO2 40 g, 5-15% methanol in chloroform)

Sources & evidence

ORD record
ord-1c00524dc7ce441ba3e511915556504a
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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