Triethylamine → HCID 23070798, compound

HRID 501448Notes

Reaction equation

HRID 501448 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:16]([N:20]1[C:24]([C:25]#[N:26])=[C:23]([C:27](O)=[O:28])[N:22]=[C:21]1[N:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)[C:17]#[C:18][CH3:19]>O1CCCC1>[CH2:16]([N:20]1[C:24]([C:25]#[N:26])=[C:23]([CH2:27][OH:28])[N:22]=[C:21]1[N:30]1[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]1)[C:17]#[C:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 23070604HCID 23070604, compound

Product 1

HCID 23070798HCID 23070798, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

6.9 g of triethylamine and then 100 ml tetrahydrofuran solution of 10.19 g of isobutyl chloroformate were added dropwise to 600 ml of tetrahydrofuran containing 22.9 g of t-butyl 4-[1-(2-butynyl)-4-carboxy-5-cyano-1H-imidazol-2-yl]piperazine-1-carboxylate at −10° C. After the precipitate had been removed by filtration, the solution was again cooled to −10° C. A 100 ml aqueous solution of 9.45 g of sodium borohydride was added dropwise to the solution. After one hour, 500 ml of ethyl acetate and 500 ml of water were added to the solution. The pH of the solution was adjusted to 5 using 1 N hydrochloric acid, and then adjusted to 10 using a saturated sodium bicarbonate solution. The organic layer was washed successively with 500 ml of water and 500 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 19.1 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (4:1).

Workup

  1. customAfter the precipitate had been removed by filtration
  2. additionA 100 ml aqueous solution of 9.45 g of sodium borohydride was added dropwise to the solution
  3. addition500 ml of ethyl acetate and 500 ml of water were added to the solution
  4. washThe organic layer was washed successively with 500 ml of water and 500 ml of a saturated sodium chloride solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-159994d87b804089b24361282a1b50b6
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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