Sodium Hydroxide → HCID 10257209, compound

HRID 441196Notes

Reaction equation

HRID 441196 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:46])[N:14]([CH2:32][C:33]([NH:35][CH:36]([CH:43]([CH3:45])[CH3:44])[C:37](=[O:42])[C:38]([F:41])([F:40])[F:39])=[O:34])[CH:15]=[C:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25]C(=O)C(C)(C)C)=[CH:21][CH:20]=2)[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:46])[N:14]([CH2:32][C:33]([NH:35][CH:36]([CH:43]([CH3:44])[CH3:45])[C:37](=[O:42])[C:38]([F:41])([F:40])[F:39])=[O:34])[CH:15]=[C:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10394405HCID 10394405, compound

Product 1

HCID 10257209HCID 10257209, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3-Benzyloxycarbonylamino-2-oxo-5-(4-pivaloyloxybenzyl)-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl]acetamide was dissolved in methanol and excess 2N sodium hydroxide was added. The mixture was allowed to stir for 3 h, was evaporated, and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed (brine), dried, evaporated and purified by chromatography, using dichloromethane:methanol (gradient, 99:1, 95:5) as the eluent, to give the title compound; NMR: 0.78-0.91 (m,6), 2.20 (m,1), 4.09 (m, NHCH hydrate), 4.50-4.77 (m,3, CH2CO, NHCH keto), 5.13 (s,2), 6.68 (d,2, J=8), 6.95 (m, OH hydrate), 6.96 (d,2, J=8), 7.20 (m,1) 7.29-7.42 (m,5), 7.70 (m,1), 7.73 (d, J=10), 8.33 (s, NH hydrate), 8.37 (S, NH keto), 8.93 (d, J=6.5, NH keto), 9.24 (s,1, OH).

Workup

  1. customwas evaporated
  2. custompartitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic layer was washed (brine)
  4. customdried
  5. customevaporated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-faf5d75c6573482bb31c3582dc376092
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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