Diisopropylethylamine → HCID 68637180, compound

HRID 2209359Notes

Reaction equation

HRID 2209359 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]([OH:10])=O)[CH2:7][CH2:6]1)=[O:4].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:44][C:45]([CH3:65])=[CH:46][CH2:47][CH2:48]/[C:49](/[CH3:64])=[CH:50]/[CH2:51][CH2:52]/[C:53](/[CH3:63])=[CH:54]/[CH2:55][S:56][CH2:57][C@H:58]([NH2:62])[C:59]([OH:61])=[O:60]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1([C:8](=[O:10])[NH:62][CH:58]([C:59]([OH:61])=[O:60])[CH2:57][S:56][CH2:55][CH:54]=[C:53]([CH3:63])[CH2:52][CH2:51][CH:50]=[C:49]([CH3:64])[CH2:48][CH2:47][CH:46]=[C:45]([CH3:65])[CH3:44])[CH2:6][CH2:7]1)=[O:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6438372FarnesylcysteineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 68637180HCID 68637180, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round bottom flask, 1,1-Cyclopropanedicarboxylic acid monomethyl ester (158 mg, 1.1 mmol), 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.1 mg, 1.1 mmol) and N,N-diisopropyl-ethyl-amine (0.52 mL, 3 mmol) were mixed in THF (5 mL). The reaction solution was stirred at room temperature for ten minutes. S-trans, trans-Farnesyl-L-cysteine (325 mg, 1 mmol) was added to reaction mixture. The reaction solution was stirred at room temperature overnight. Ethyl acetate (50 mL) was added and then washed with saturated ammonium chloride aqueous solution (20 mL×2), DI water (20 mL×2) and brine (20 mL×2) sequentially. The ethyl acetate solution was dried by Na2SO4 and concentrated in vacuo to afford crude Compound N-52. The crude Compound N-52 was purified by HPLC (120 mg, 27%) to yield Compound N-52. 1H-NMR (500 MHz, MeOH-d4): δ 1.45-1.48 (m, 4H), 1.50 (s, 6H), 1.57 (s, 3H), 1.58 (s, 3H), 1.85-1.89 (m, 2H), 1.93-1.98 (m, 4H), 2.01-2.05 (m, 2H), 2.78-2.91 (m, 2H), 3.06-3.15 (m, 2H), 3.62 (s, 3H), 4.56 (t, J=5.0 Hz, 1H), 4.97-5.02 (m, 2H), 5.12 (t, J=7.5 Hz, 1H). 13C-NMR (125 MHz, MeOH-d4): δ 9.2, 16.14, 16.20, 17.80, 20.05, 25.95, 27.31, 27.37, 27.78, 30.61, 33.62, 40.74, 40.88, 52.96, 53.97, 121.61, 125.11, 125.45, 132.11, 136.28, 140.59, 170.81, 173.75, 174.39; ES-MS: mass calcd for Chemical Formula: C24H37NO5S 451.2. Found (M+Na) m/z 474.2.

Workup

  1. stirringThe reaction solution was stirred at room temperature overnight
  2. washwashed with saturated ammonium chloride aqueous solution (20 mL×2), DI water (20 mL×2) and brine (20 mL×2) sequentially
  3. dry with materialThe ethyl acetate solution was dried by Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto afford crude Compound N-52
  6. customThe crude Compound N-52 was purified by HPLC (120 mg, 27%)
  7. customto yield Compound N-52

Sources & evidence

ORD record
ord-0909d0512e0a48a997228e51c167f202
Source dataset
uspto-grants-2016_06
Patent number
US09376383B2

Reaction notes

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