Methyl iodide → HCID 131723724, compound

HRID 2300964Notes

Reaction equation

HRID 2300964 reaction equation
[C:1]([O:5][C:6](=[O:31])[O:7][C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][C@@H:13]([SH:18])[C@H:12]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:11]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:10]=2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].IC.[C:34](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:31])[O:7][C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][C@@H:13]([S:18][CH3:34])[C@H:12]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:11]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:10]=2[CH:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 131723723HCID 131723723, compound

Product 1

HCID 131723724HCID 131723724, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of carbonic acid 7-tert-butoxycarbonylamino-8,8-diethyl-trans-6-mercapto-5,6,7,8-tetrahydro-naphthalen-2-yl ester tert-butyl ester (28.2 mg, 0.062 mmol) in acetone (2 mL) was added the iodomethane (20 μL, 0.31 mmol) and the potassium carbonate (26 mg, 0.18 mmol), and stirred at reflux for 4 h. The mixture was quenched with H2O, diluted with Et2O (50 mL), washed with H2O, brine, dried over MgSO4. The residu was purified by a flash chromatography (10% AcOEt/Hex) (21.2 mg , 73%). 1H NMR (CDCl3): 7.08 (1H, d, J=8.5 Hz, H5), 7.00-6.95 (2H, m, H6 and H8), 4.56 (1H, d, J=11 Hz, NH), 4.09 (1H, t, J=11.0 Hz, CHNH), 3.25-3.00 (3H, m), 2.15 (3H , broad, SCH3), 1.76 (4H, m, CH2), 1.57 (9H, s, t-butyl), 1.50 (9H, s, t-butyl), 0.73 (6H, m, CH3).

Workup

  1. temperatureat reflux for 4 h
  2. customThe mixture was quenched with H2O
  3. additiondiluted with Et2O (50 mL)
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. customThe residu was purified by a flash chromatography (10% AcOEt/Hex) (21.2 mg , 73%)

Sources & evidence

ORD record
ord-920484da09fd44ab94e43bb41acd4ddc
Source dataset
uspto-grants-2002_12
Patent number
US06498196B1

Reaction notes

Loading…