Isopropyl chloroformate → N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinol

HRID 1627467Notes

Reaction equation

HRID 1627467 reaction equation
C(Cl)(=O)OC(C)C.[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([NH:15][C:16]1([C:22]([NH:24][C@H:25]([C:29](O)=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:14].C(N(CC)CC)C.[BH4-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([NH:15][C:16]1([C:22]([NH:24][C@H:25]([CH2:29][OH:30])[CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:14]

Participants

8

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 24737720N-[[1-[(2-furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valine

Product 1

HCID 24876087N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinolYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 72 mg (0.59 mmol) of isopropyl chlorocarbonate was added to a solution of 200 mg (0.59 mmol) of N-[[1-[(2-furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valine and 60 mg (0.59 mmol) of triethylamine in 2 ml of tetrahydrofuran under ice-cooling. After the mixture was stirred at 0° C. for 2 hours, the reaction solution was filtered and poured to a solution of 45 mg (1.2 mmol) of sodium borohydride in 1 ml of water, and the mixture was stirred overnight. Ethyl acetate was added to the reaction solution, and the mixture was successively washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained crystal was washed with ether to obtain 30 mg (16%) of the title compound.

Workup

  1. temperaturecooling
  2. filtrationthe reaction solution was filtered
  3. stirringthe mixture was stirred overnight
  4. washthe mixture was successively washed with a 10% aqueous potassium hydrogensulfate solution
  5. dry with materialby drying with sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. washthe obtained crystal was washed with ether

Sources & evidence

ORD record
ord-f6484c0539f7410fa554503a782cdb29
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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