Hydrochloric Acid → HCID 46207468, compound

HRID 2209339Notes

Reaction equation

HRID 2209339 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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of S-trans, trans-farnesyl-L-cysteine (500 mg, 1.54 mmol) in THF and a 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) portionwise while maintaining the pH at 9.0-10.0 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 2.0 by the addition of 2 N 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 Na2SO4 and then concentrated to afford crude Compound A, which was further purified by preparative HPLC (552 mg, 85%) to yield Compound A. 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. 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 Na2SO4
  6. concentrationconcentrated
  7. customto afford crude Compound A, which
  8. customwas further purified by preparative HPLC (552 mg, 85%)

Sources & evidence

ORD record
ord-b6a8cc2c5b024a3697a4db6ffad8fca4
Source dataset
uspto-grants-2016_06
Patent number
US09376383B2

Reaction notes

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