Sodium Hydroxide → HCID 66744596, compound

HRID 1959482Notes

Reaction equation

HRID 1959482 reaction equation
[C:1]([O:5][C:6]([N:8]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:9]1[N:10]=[CH:11][C:12]([CH:36]2[CH2:38][CH:37]2[C:39]([O:41]CC)=[O:40])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[C:47]([O:46][C:44]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[N:10]=[CH:11][C:12]([CH:36]2[CH2:38][CH:37]2[C:39]([OH:41])=[O:40])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:24][CH:25]=2)=[N:18][N:19]=1)=[O:45])([CH3:48])([CH3:49])[CH3:50]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66744808HCID 66744808, compound

Product 1

HCID 66744596HCID 66744596, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylate (825 mg, 1.2 mmol) in THF:MeOH solvent mixture (3.2 mL:1.6 mL) at room temperature was added aqueous NaOH (594 μL, of 4 M, 2.37 mmol) and reaction mixture was heated at 50° C. for 20 minutes. The reaction mixture was cooled to room temperature and diluted with EtOAc and washed with 1M HCl solution. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to obtain 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ 10.19 (s, 1H), 8.73 (s, 1H), 8.07 (d, J=8.2 Hz, 2H), 7.47 (t, J=6.7 Hz, 2H), 4.49 (s, 2H), 2.83 (s, 5H), 1.91 (s, 2H), 1.49-1.33 (m, 27H). LC/MS m/z 567.6 [M+H]+. (less 1 Boc)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 1M HCl solution
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e49301a8900b44cf97e8586ea55c0c58
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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