Formic Acid → HCID 22874822, compound

HRID 342814Notes

Reaction equation

HRID 342814 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([C:16]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:26]([OH:28])=O.[CH:29]1([N+:35]#[C-])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH3:37][OH:38]>>[CH:29]1([NH:35][C:26](=[O:28])[C@:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]([CH:37]=[O:38])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 887MethanolHCID 7504BenzylamineHCID 79129Cyclohexyl isocyanideHCID 56208237985-17-4

Product 1

HCID 22874822HCID 22874822, compound

Procedure

Bzl-NH2 288 μl (2.64 mmol) and benzyl phenethylketone 592 mg (2.64 mmol) were dissolved in MeOH (5 ml) at rt and the solution was stirred overnight. To the mixture were added formic acid 99.6 μl (2.64 mmol) and cyclohexylisocyanide 298 μl (2.4 mmol) at rt, which was allowed to react at rt for 2 weeks. Insoluble material in MeOH was collected by filtration and washed with MeOH, ether and then n-hexane. The crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane. Yield 540 mg (48.2%), NMR in CDCl3 ; δ=0.8-1.8 cyclohexyl (11H), δ=2.1-4.75 CH2 (8H), δ=5.45-5.55 NH (1H), δ=7.0-7.4 phenyl (15H), δ=8.25 (main) and 8.4 (minor) formyl (1H).

Workup

  1. customto react at rt for 2 weeks
  2. filtrationInsoluble material in MeOH was collected by filtration
  3. washwashed with MeOH, ether
  4. customThe crude product was recrystallized from CHCl3 with the 2 to 1 mixture of ether and n-hexane

Sources & evidence

ORD record
ord-2285a32a18e14bcdb1532c8a9f2f5e01
Source dataset
uspto-grants-1999_01
Patent number
US05858979

Reaction notes

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