Hydrazine → HCID 42611128, compound

HRID 1482466Notes

Reaction equation

HRID 1482466 reaction equation
[C:1]([NH:4][C@H:5]([C:23]([OH:25])=O)[CH2:6][S:7][CH2:8][CH:9]=[C:10]([CH2:12][CH2:13][CH:14]=[C:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:16])[CH3:11])(=[O:3])[CH3:2].[NH2:26][NH2:27]>ClCCl.C1COCC1>[NH:26]([C:23](=[O:25])[C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][S:7][CH2:8]/[CH:9]=[C:10](\[CH3:11])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:16])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[NH2:27]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 121840HCID 121840, compound

Product 1

HCID 42611128HCID 42611128, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In 50 mL round bottom flask, N-acetyl-S-farnesyl-L-cysteine (368 mg, 1.0 mmole) was dissolved in dichloromethane (10 mL). N-Cyclohexylcarbodiimide,N′-methyl polystyrene HL (1.7 g, 3.3 mole, from NovabioChem) was added followed by sufficient dichloromethane to swell the resin and keep the reaction mobile and the mixture gently magnetically stirred in 30 minutes. 5 mL of hydrazine in THF (1M) was added to the reaction solution and the reaction mixture was stirred in 3 hours at room temperature. The used resin was removed by filtration and washed with dichloromethane. Evaporation of the filtrate provided crude reaction mixture. The desired product was purified by preparative HPLC (305 mg, 80% yield) to yield Compound I: 1H-NMR (500 MHz, CDCl3): δ 1.60 (s, 6H), 1.67 (s, 6H), 1.70 (S, 3H), 1.92-2.09 (m, 8H), 2.75 (dd, J=7.9, 13.9 Hz, 1H), 2.88 (dd, J=5.7, 13.6 Hz, 1H), 3.20 (d, J=7.9 Hz, 2H), 4.51 (dd, J=7.6, 13.6 Hz, 1H), 5.10 (m, 2H), 5.24 (t, J=7.6 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ 16.0, 16.1, 16.2, 17.6, 17.7, 23.2, 23.4, 23.5, 25.7, 25.8, 26.2, 26.3, 26.5, 26.7, 30.0, 31.8, 31.9, 32.9, 33.2, 39.6, 39.7, 39.9, 51.3, 51.4, 119.6, 120.3, 123.6, 124.2, 131.4, 131.6, 135.5, 135.6, 135.8, 140.2, 140.3, 170.2, 171.1; ES-MS: mass calcd for Chemical Formula: C20H35N3O2S 381.2 (M+). Found (M+Na) m/z 404.3.

Workup

  1. stirringthe reaction mixture was stirred in 3 hours at room temperature
  2. customThe used resin was removed by filtration
  3. washwashed with dichloromethane
  4. customEvaporation of the filtrate
  5. customprovided crude
  6. customreaction mixture
  7. customThe desired product was purified by preparative HPLC (305 mg, 80% yield)

Sources & evidence

ORD record
ord-3c3eea18f4b546888b667c75ea031d76
Source dataset
uspto-grants-2016_08
Patent number
US09415026B2

Reaction notes

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