Isopropyl iodide → N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl ester

HRID 343324Notes

Reaction equation

HRID 343324 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=1)[NH:6][S:7]([C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][NH:16][CH2:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].I[CH:31]([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=1)[NH:6][S:7]([C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][N:16]([CH:31]([CH3:33])[CH3:32])[CH2:17]2)=[CH:12][CH:11]=1)(=[O:8])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 54386742N-(1,2,3,4-Tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

Product 1

HCID 22885593N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl esterYield 74.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of N-(1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester (Preparation 23; 1.3 g, 3.14 mmol), 2-iodopropane (641 mg, 377 μl, 3.77 mmol), potassium carbonate (650 mg, 4.7 mmol) and acetonitrile (50 ml) was heated under reflux for 9 hours, more 2-iodopropane (35 μl) added and heating under reflux continued for 1 hour. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica gel, using a 0-5% methanol in dichloromethane elution gradient, followed by trituration with diisopropyl ether, to afford the title compound (1.07 g) as a white solid, m.p. 110° C. Rf 0.49 (SS 6). Found: C,63.19; H,6.34; N,8.89. C24H29N3O4S requires C,63.27; H,6.41; N,9.22%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 9 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue purified by chromatography on silica gel
  7. washa 0-5% methanol in dichloromethane elution gradient

Sources & evidence

ORD record
ord-d4aab6f6c7314f22bd52eb49f346bb5d
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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