HCID 67265665, compound → HCID 67265683, compound

HRID 1685754Notes

Reaction equation

HRID 1685754 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][NH:6][C:7](=[O:36])[CH2:8][CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[N:21]=[C:20]([C:22]3[S:23][C:24]([CH2:28][N:29]([CH:31]([CH3:33])[CH3:32])[CH3:30])=[C:25]([CH3:27])[CH:26]=3)[O:19][N:18]=2)=[CH:12][C:11]=1[CH2:34][CH3:35])C>C(O)C.[OH-].[Na+]>[CH2:34]([C:11]1[CH:12]=[C:13]([C:17]2[N:21]=[C:20]([C:22]3[S:23][C:24]([CH2:28][N:29]([CH:31]([CH3:33])[CH3:32])[CH3:30])=[C:25]([CH3:27])[CH:26]=3)[O:19][N:18]=2)[CH:14]=[C:15]([CH3:16])[C:10]=1[CH2:9][CH2:8][C:7]([NH:6][CH2:5][C:4]([OH:37])=[O:3])=[O:36])[CH3:35]

Participants

4

Reactant 1

HCID 67265665HCID 67265665, compound

Product 1

HCID 67265683HCID 67265683, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of {3-[2-ethyl-4-(5-{5-[(isopropyl-methyl-amino)-methyl]-4-methyl-thiophen-2-yl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenyl]-propionylamino}-acetic acid ethyl ester (5 mg, 9 μmol) in ethanol (500 μL) and 1 N aq. NaOH (100 μL) is stirred at rt for 1 h before it is concentrated, diluted with formic acid (1 mL) and separated by prep. HPLC (column: Atlantis T3 C18, 30×75 mm, 10 μm, eluting with a gradient of acetonitrile in water containing 0.5% of formic acid) to give the title compound (4 mg) as a resin; LC-MS*: tR=0.66 min; [M+1]+=498.97, 1H NMR (D6-DMSO): δ 1.05 (d, J=6.5 Hz, 6H), 1.23 (t, J=7.3 Hz, 3H), 2.23 (s, 6H), 2.28-2.35 (m, 2H), 2.41 (s, 3H), 2.74 (q, J=7.5 Hz, 2H), 2.87-2.98 (m, 3H), 3.70 (s, 2H), 3.76 (d, J=5.5 Hz, 2H), 7.69 (s, 2H), 7.81 (s, 1H), 8.23 (t br, J=5.5 Hz).

Workup

  1. concentrationis concentrated
  2. additiondiluted with formic acid (1 mL)
  3. customseparated by prep
  4. washHPLC (column: Atlantis T3 C18, 30×75 mm, 10 μm, eluting with a gradient of acetonitrile in water containing 0.5% of formic acid)

Sources & evidence

ORD record
ord-b161d3ac6a1746ee8544f773ab81df7a
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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