Sodium Hydroxide → HCID 71769324, compound

HRID 515398Notes

Reaction equation

HRID 515398 reaction equation
[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH:23]5[O:28][CH2:27][CH:26]([CH2:29][C:30]([O:32]C)=[O:31])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)=[N:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+:35].[Na]>C1COCC1.CO.O>[Na+:35].[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH:23]5[O:28][CH2:27][CH:26]([CH2:29][C:30]([O-:32])=[O:31])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[N:7][N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 89872736HCID 89872736, compound

Product 1

HCID 71769324HCID 71769324, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-(6-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)tetrahydro-2H-pyran-3-yl)acetate (43 mg, 0.10 mmol) in THF (0.5 ml) and MeOH (0.5 ml) was added a solution of 1N NaOH (0.29 ml, 0.29 mmol). The mixture was stirred at room temperature for overnight. Afterward, the reaction mixture was concentrated to dryness afford a white solid. The solid was taken up in water to form a slurry and was subsequently filtered. The filtercake was washed with water, dried to afford the title compound (36 mg, 81% yield) as a sodium salt. The ratio of cis to trans isomer was determined to be ˜1:1.2 by NMR studies. HR/MS [M+H]+: found 434.2071, calc. 434.2080. RT: 1.72 (Condition L). HR/MS [M+H]+: found 434.2077, calc. 434.2080. RT: 1.75 (Condition L).

Workup

  1. concentrationAfterward, the reaction mixture was concentrated to dryness
  2. customafford a white solid
  3. customto form a slurry
  4. filtrationwas subsequently filtered
  5. washThe filtercake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-91c08457e8f24944ad0ab1d2f43b4061
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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