Methanol → HCID 53747152, compound

HRID 1637114Notes

Reaction equation

HRID 1637114 reaction equation
[NH2:1][CH2:2][CH:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:13]=1)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC.[CH3:33][C:34](OC(C)=O)=[O:35].CO>CCOC(C)=O>[CH:21]1([O:20][C:14]2[CH:13]=[C:12]([CH:3]([C:4]#[C:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:2][NH:1][C:34](=[O:35])[CH3:33])[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 536406913-(Cyclopentyloxy)-4-methoxy-β-(2-phenylethynyl)benzeneethanamine

Product 1

HCID 53747152HCID 53747152, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (+/-)-4-amino-3-(3 cyclopentyloxy-4-methoxyphenyl)-1-phenyl-1-butyne (50 mg, 0.15 mmol) and Et3N (0.2 ml) in EtOAc (30 ml) at 5° was treated with Ac2O (0.2 ml). After 5 minutes, the reaction was treated with MeOH, to decompose excess Ac2O. The reaction was washed with H2O and 0.05 N HCl, dried, and the solvent was evaporated. The residue was purified by flash chromatography (alumina, neutral, activity 1, 5% MeOH/CHCl3), and then by recrystallization from a mixture of cyclohexane and Et2O, and gave the titled compound, 37 mg (65%). mp 114-117°. 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.32 (m, 3 H), 6.92 (m, 2 H), 6.84 (d, 1 H), 5.78 (broad s, 1 H), 4.76 (m, lH), 4.02 (t, 1 H), 3.82 (s, 3 H), 3.64 (m, 1 H), 3.50 (m, 1 H), 2.06 (s, 3 H), 1.78-2.00 (m, 6 H), 1.62 (m, 2 H).

Workup

  1. washThe reaction was washed with H2O and 0.05 N HCl
  2. customdried
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography (alumina, neutral, activity 1, 5% MeOH/CHCl3)
  5. customby recrystallization
  6. additionfrom a mixture of cyclohexane and Et2O

Sources & evidence

ORD record
ord-36656eb9f73b440a923c7b9e486e617c
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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