Hydrochloric Acid → N-Succinyl-S-farnesyl-L-cysteine

HRID 1256679Notes

Reaction equation

HRID 1256679 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])[CH2:31][CH2:30]1.Cl>C1COCC1>[C:16]([C@@H:15]([NH:19][C:29](=[O:35])[CH2:30][CH2:31][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 7922Succinic anhydrideHCID 11430Potassium Carbonate2×HCID 6438372Farnesylcysteine

Product 1

HCID 46207469N-Succinyl-S-farnesyl-L-cysteineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-trans, trans-farnesyl-L-cysteine (500 mg, 1.54 mmol) in THF and first portion of K2CO3 (2 mmol) was cooled to 5° C. with vigorous stirring. To this stirred solution was added succinic anhydride (308 mg, 3.1 mmol) drop wise while maintaining the PH at 9-10 with another portion of K2CO3 (4 mmol). The mixture was stirred at room temperature for 2 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 10 ml of ethyl acetate. The combined organic extract was washed with water, brine and dried over sodium sulfate, the solvent was removed on rotary evaporator to afford crude product, which was further purified by preparative HPLC (535 mg, 82% yield): 1H-NMR (500 MHz, CDCl3) δ 1.59 (s, 6H), 1.66 (s, 6H), 2.05 (m, 8H), 2.60 (m, 2H), 2.48 (m, 2H), 2.86 (dd, 1H), 2.94 (dd, 1H), 3.10 (dd, 1H), 3.12 (dd, 1H), 4.68 (dd, 1H), 5.06 (m, 2H), 5.20 (t, 1H); 13C-NMR (125 MHz, CDCl3) δ 16.0, 16.1, 17.7, 25.7, 26.5, 26.7, 29.4, 29.8, 30.5, 32.6, 39.6, 39.7, 52.2, 119.3, 123.8, 124.3, 131.3, 135.4, 140.3, 173.4, 174.2, 176.8; ES-MS: mass calcd for Chemical Formula: C22H35NO5S 425.6 (M+). Found (M+Na) m/z 448.

Workup

  1. customcompletion of the reaction
  2. extractionThe acidic solution was extracted three times with 10 ml of ethyl acetate
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed on rotary evaporator
  7. customto afford crude product, which
  8. customwas further purified by preparative HPLC (535 mg, 82% yield)

Sources & evidence

ORD record
ord-a4ff517e045144e3a790fed151119d20
Source dataset
uspto-grants-2013_06
Patent number
US08461204B2

Reaction notes

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