Hydrochloric Acid → HCID 178436577, compound

HRID 1713745Notes

Reaction equation

HRID 1713745 reaction equation
O.[OH-].[Li+].[CH2:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[O:17][C:16]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C@H:27]4[CH2:32][CH2:31][C@H:30]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)=[O:19])=[N:15][N:14]=2)=[CH:8][CH:7]=1)[CH3:5].Cl>O.C1COCC1.CO>[CH2:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[O:17][C:16]([C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C@H:27]4[CH2:32][CH2:31][C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:29][CH2:28]4)=[CH:25][CH:26]=3)=[O:19])=[N:15][N:14]=2)=[CH:8][CH:7]=1)[CH3:5]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178436578HCID 178436578, compound

Product 1

HCID 178436577HCID 178436577, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (110 mg, 2.64 mmol.) in water (1.4 mL) was added to a suspension of methyl (trans-4-{4-[({5-[(4-ethylphenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetate (152 mg, 0.33 mmol) in THF (1.6 mL) and MeOH (2.6 mL). After 24 h, 1M aqueous HCl (5 mL) was added followed by water (10 mL). The solid was filtered off and washed with water (2×5 mL), Et2O (2×5 mL) then hexane (2×5 mL) to give the title compound as a solid (105 mg, 71%); 1H NMR δ 1.04-1.19 (5H, m), 1.37-1.51 (2H, m), 1.65-1.85 (5H, m), 2.11-2.15 (2H, m), 2.39-2.47 (1H, m), 2.57 (2H, q), 7.21 (4H, m), 7.49 (2H, d), 7.68 (2H, d), 10.84 (1H, s), 10.91 (1H, s), 11.99 (1H, s); MS m/e MH+ 449.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water (2×5 mL), Et2O (2×5 mL)

Sources & evidence

ORD record
ord-fef595e723a049428a91c46a0b299fb8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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