Hydrochloric Acid → HCID 46207468, compound

HRID 1256680Notes

Reaction equation

HRID 1256680 reaction equation
[CH3:1][C:2]([CH3:22])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:21])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:20])=[CH:11]/[CH2:12][S:13][CH2:14][C@H:15]([NH2:19])[C:16]([OH:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[C:29]1(=[O:35])[O:34][C:32](=[O:33])[CH:31]=[CH:30]1.Cl>C1COCC1>[C:16]([C@@H:15]([NH:19][C:29](=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33])[CH2:14][S:13][CH2:12]/[CH:11]=[C:10](\[CH3:20])/[CH2:9][CH2:8]/[CH:7]=[C:6](\[CH3:21])/[CH2:5][CH2:4][CH:3]=[C:2]([CH3:22])[CH3:1])([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 11430Potassium Carbonate2×HCID 6438372Farnesylcysteine

Product 1

HCID 46207468HCID 46207468, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of S-trans, trans-farnesyl-L-cysteine (500 mg, 1.54 mmol) in THF and first portion of K2CO3 (3 mmol) was cooled to 5° C. with vigorous stirring. To this stirred solution was added maleic anhydride (302 mg, 3.07 mmol) portions wise while maintaining the PH at 9-10 with another portion of K2CO3 (3 mmol). The mixture was stirred at room temperature for 3 h, HPLC analysis showed completion of the reaction. The pH of the reaction mixture then adjusted to 2 by the addition of 2N HCl solution. The acidic solution was extracted three times with 15 ml of ethyl acetate. The combined organic extract was washed with water, brine and dried over sodium sulfate and then concentrated to afford crude product, which was further purified by preparative HPLC (552 mg, 85% yield): 1H-NMR (500 MHz, CD3OD) δ 1.50 (bs, 6H), 1.57 (s, 3H), 1.59 (s, 3H), 1.85-2.10 (m, 8H), 2.68 (dd, J=6.5, 14.5, 1H), 2.95 (dd, J=4.5, 14.0 Hz, 1H), 3.07 (dd, J=7.0, 13.0 Hz, 1H), 3.17 (dd, J=8.5, 13.5 Hz, 1H), 4.59 (dd, J=4.5, 8.5), 4.97-5.02 (m, 2H), 5.12 (t, J=7.5, 1H), 6.21 (d, J=13.0 Hz, 1H), 6.47 (d, J=13.0 Hz, 1H); 13C-NMR (125 MHz, CDCl3) δ 16.2, 16.3, 17.8, 25.3, 26.0, 27.4, 27.8, 30.3, 33.3, 40.8, 40.9, 54.0, 121.5, 125.1, 125.5, 132.1, 133.3, 134.4, 136.3, 140.7, 167.7, 168.0, 172.9; ES-MS: mass calcd for Chemical Formula: C22H33NO5S 423.6 (M+). Found (M+Na) m/z 446.

Workup

  1. customcompletion of the reaction
  2. extractionThe acidic solution was extracted three times with 15 ml of ethyl acetate
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford crude product, which
  8. customwas further purified by preparative HPLC (552 mg, 85% yield)

Sources & evidence

ORD record
ord-9081091e16a0436bbc67e60c17db2716
Source dataset
uspto-grants-2013_06
Patent number
US08461204B2

Reaction notes

Loading…