4-Penten-1-OL → HCID 86683900, compound

HRID 409641Notes

Reaction equation

HRID 409641 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:26](O)[CH2:27][CH2:28][CH:29]=[CH2:30]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:10])[C:11]([O:13][CH2:30][CH2:29][CH2:28][CH:27]=[CH2:26])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 131814-Penten-1-OLHCID 682631,1'-CarbonyldiimidazoleHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 86683900HCID 86683900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(t-Butoxycarbonyl)alanine (3.1 g, 1 eq) and DCM (50 mL) were added to a vessel with stirring followed by the addition of CDI (3.1 g, 1.15 eq). The mixture was stirred at ambient temperature for 18 h after which time 4-penten-1-ol (1.8 g, 1.25 eq) was added. The mixture was stirred a further 18 h at ambient temperature at which point the reaction was quenched with 1N HCl. A biphasic mixture was formed and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 solution and then concentrated to give pent-4-en-1-yl 2-((tert-butoxycarbonyl)amino)propanoate as an oil. The oil was dissolved in DCM (50 mL) and methanesulfonic acid (2.2 g, 1.4 eq) was added. The mixture was stirred at ambient temperature for ˜22 h then cooled in an ice/water bath. Ethyl 2-chloro-2-oxoacetate (3.4 g, 1.5 eq) was added followed by drop-wise addition of triethylamine (5.0 g, 3 eq). The mixture was stirred for 7 h after which time the reaction was quenched by 1N HCl to form a biphasic mixture. The layers were separated and the organic layer was washed with a saturated aqueous NaHCO3 solution. The organic layer was then concentrated under reduced pressure to provide pent-4-en-1-yl 2-(2-ethoxy-2-oxoacetamido)propanoate as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (d, J=6.94 Hz, 1H), 5.66-5.83 (m, 1H), 4.90-5.05 (m, 2H), 4.49-4.62 (m, 1H), 4.31 (qd, J=7.17, 2.26 Hz, 2H), 4.13 (td, J=6.59, 2.13 Hz, 2H), 2.02-2.14 (m, 2H), 1.67-1.78 (m, 2H), 1.44 (d, J=7.19 Hz, 3H), 1.34 (t, J=7.15 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 171.64, 159.94, 155.83, 136.94, 115.40, 64.98, 63.10, 48.40, 29.71, 27.44, 17.88, 13.80; HRMS (M+Na) m/z, calcd for C12H19NO5Na, 280.1161; found, 280.1166.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred a further 18 h at ambient temperature at which
  3. customwas quenched with 1N HCl
  4. customA biphasic mixture was formed
  5. customthe layers were separated
  6. washThe organic layer was washed with saturated aqueous NaHCO3 solution
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2123af473766479182e019f9c90ba3f8
Source dataset
uspto-grants-2014_06
Patent number
US08759523B2

Reaction notes

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