Ethanol → HCID 54108949, compound

HRID 1637116Notes

Reaction equation

HRID 1637116 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:16][NH:17][C:18](=[O:23])[C:19]([O:21]C)=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH3:34]CO>O>[CH3:34][N:17]([CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[C:24]#[C:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18](=[O:23])[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 19349944HCID 19349944, compound

Product 1

HCID 54108949HCID 54108949, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (+,-)-methyl 2-(3-cyclopentyloxy-4-methoxyphenyl)-4-phenyl-but-3-ynyloxamate (100 mg, 0.24 mmol) in hot EtOH (3 ml) was treated with 2.5N NaOH (0.5 ml). The reaction was diluted with H2O, acidified with Hcl, and extracted with EtOAc. The extracts were washed with H2O, dried and the solvent evaporated. The residue was recrystallized from MeCN, and gave the titled compound, 42 mg (44%). mp 157-159°. 1H NMR (400 MHz, CDCl3 +DMSO-D6) δ 7.63 (t, 1 H), 7.45 (m, 2 H), 7.30 (m, 4 H), 6.97 (m, 2 H), 6.85 (d, 1 H), 4.79 (m, 1 H), 4.07 (t, 1 H), 3.84 (s, 3 H), 3.74 (m, 1 H), 3.62 (m, 1 H), 1.78-1.98 (m, 6 H), 1.61 (m, 2 H).

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts were washed with H2O
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was recrystallized from MeCN

Sources & evidence

ORD record
ord-7313dc97bf7c4df8b8e6b8e1b4b691f5
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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