Hydrochloric Acid → HCID 20503645, compound

HRID 850974Notes

Reaction equation

HRID 850974 reaction equation
[C:1]([NH:18][C:19]1[CH:20]=[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:22]([CH3:24])[CH:23]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([NH:18][C:19]1[CH:20]=[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:22]([CH3:24])[CH:23]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 20503610HCID 20503610, compound

Product 1

HCID 20503645HCID 20503645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g. of ethyl 4-hexadecanamido-1-methyl-2-pyrrolecarboxylate in 10 ml. of dry tetrahydrofuran is added dropwise to a solution of 6 ml. of 1 M borane in tetrahydrofuran under nitrogen and the pale yellow solution is heated to reflux overnight. After cooling and acidification with 1 N aqueous hydrochloric acid followed by neutralization with saturated sodium bicarbonate solution, the solution is extracted with ether. The extract is dried over anhydrous magnesium sulfate and evaporated. The residue is recrystallized from hexane to yield the product as a white solid.

Workup

  1. temperatureto reflux overnight
  2. temperatureAfter cooling
  3. extractionthe solution is extracted with ether
  4. dry with materialThe extract is dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-a812df4ac6d144e78e525d297004f975
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

Loading…