Diisopropylethylamine → HCID 46208242, compound

HRID 388170Notes

Reaction equation

HRID 388170 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH3:8][C:9]([CH3:29])=[CH:10][CH2:11][CH2:12]/[C:13](/[CH3:28])=[CH:14]/[CH2:15][CH2:16]/[C:17](/[CH3:27])=[CH:18]/[CH2:19][S:20][CH2:21][C@H:22]([NH2:26])[C:23]([OH:25])=[O:24].C(N(CC)C(C)C)(C)C>C1COCC1.C(OCC)(=O)C>[CH:1]1([S:4]([NH:26][C@@H:22]([CH2:21][S:20][CH2:19]/[CH:18]=[C:17](\[CH3:27])/[CH2:16][CH2:15]/[CH:14]=[C:13](\[CH3:28])/[CH2:12][CH2:11][CH:10]=[C:9]([CH3:29])[CH3:8])[C:23]([OH:25])=[O:24])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 6438372Farnesylcysteine

Product 1

HCID 46208242HCID 46208242, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round bottom flask, to a suspension of cyclopropanesulfonyl chloride (169 mg, 1.2 mmol) and S-trans, trans-farnesyl-L-cysteine (325 mg, 1 mmol) in THF (5 mL) was added N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol) dropwise. The solution was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (60 mL) and washed by 0.5 N HCl (10 mL×1), H2O (10 mL×2) and brine (10 mL×1). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was then further purified by preparative HPLC (50 mg, 12%) to yield Compound N-79. 1H-NMR (500 MHz, CD3OD): δ 0.86-0.89 (m, 2H), 0.93-0.96 (m, 2H), 1.50 (s, 3H), 1.51 (s, 3H), 1.57 (s, 3H), 1.61 (s, 3H), 1.86-1.89 (m, 2H), 1.95-1.98 (m, 4H), 2.00-2.04 (m, 2H), 2.43-2.46 (m, 1H), 2.66-2.68 (m, 1H), 2.76-2.79 (m, 1H), 3.09-3.13 (m, 1H), 3.16-3.21 (m, 1H), 4.02 (t, J=5.0 Hz, 1H), 4.99-5.01 (m, 2H), 5.15 (t, J=5.0 Hz, 1H). 13C-NMR (125 MHz, CD3OD): δ 5.58, 6.28, 16.16, 16.30, 17.81, 25.96, 27.39, 27.80, 30.41, 31.73, 34.88, 40.79, 40.90, 57.75, 121.67, 125.17, 125.47, 132.12, 136.28, 140.55, 174.39; ES-MS: mass calcd for Chemical Formula: C21H35NO4S2 429.64. Found (M+) m/z 430.2, (M+Na) m/z 452.2.

Workup

  1. washwashed by 0.5 N HCl (10 mL×1), H2O (10 mL×2) and brine (10 mL×1)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was then further purified by preparative HPLC (50 mg, 12%)
  5. customto yield Compound N-79

Sources & evidence

ORD record
ord-1866e5ca96fd48cc88c7bc6e7a91e090
Source dataset
uspto-grants-2013_02
Patent number
US08372884B2

Reaction notes

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