Sodium Hydroxide → HCID 44413446, compound

HRID 1443422Notes

Reaction equation

HRID 1443422 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:10][C@@H:9]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:31][CH:30]=3)[O:26][N:25]=2)=[CH:20][CH:19]=1)=O)(C)(C)C.[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:35]1([C:32]2[CH:33]=[CH:34][C:29]([C:27]3[O:26][N:25]=[C:24]([C:21]4[CH:22]=[CH:23][C:18]([C@H:9]5[CH2:10][C@H:11]([CH2:13][C:14]([OH:16])=[O:15])[CH2:12][NH:8]5)=[CH:19][CH:20]=4)[N:28]=3)=[CH:30][CH:31]=2)[CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68665546HCID 68665546, compound

Product 1

HCID 44413446HCID 44413446, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl trans-N-tert-butyloxycarbonyl-2-(4-(5-(4-cyclopentylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)-4-pyrrolidineacetate (4.4 mg, 8.3 μmol) in 2.5 mL of 20% TFA in CH2Cl2 was stirred at rt for 1 hr and then concentrated. The residue was redissolved in 5.0 mL of EtOH and sodium hydroxide (189 μL, 5.0 N, 0.95 mmol) was added. After stirring at rt for 1 hr, the reaction mixture was concentrated and the residue was purified on HPLC to give 3.5 mg (100%) of the title compound: 1H NMR (CD3OD) δ 1.60 (m, 214), 1.69 (m, 2H), 1.81 (m, 2H), 2.06 (m, 2H), 2.26 (m, 1H), 2.46 (m, 1H), 2.58 (m, 2H), 2.96 (m, 1H), 3.07 (m, 1H), 3.12 (dd, J=7.7, 11.9, 1H), 3.70 (dd, J=7.7, 11.8, 1H), 4.84 (t, J=8.6, 1H), 7.44 (d, J=8.2, 2H), 7.60 (d, J=8.4, 2H), 8.06 (d, J=8.4, 2H), 8.18 (d, J=8.2, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in 5.0 mL of EtOH
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was purified on HPLC

Sources & evidence

ORD record
ord-932a0db3a1c848009318b78ab9e02dbe
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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