Cyclohexylamine → HCID 131724641, compound

HRID 2414809Notes

Reaction equation

HRID 2414809 reaction equation
[CH3:1][C@@H:2]1[CH2:20][C@H:19]([CH3:21])[C@@H:18]([OH:22])[CH2:17][C:15](=[O:16])[O:14][C@H:13]([C@H:23]2[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH2:24]2)[CH2:12][CH:11]=[CH:10][CH:9]=[C:8]([C:31]#[N:32])[C@H:7]([OH:33])[C@@H:6]([CH3:34])[CH2:5][C@H:4]([CH3:35])[CH2:3]1.[CH:36]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C@@H:2]1[CH2:20][C@H:19]([CH3:21])[C@@H:18]([OH:22])[CH2:17][C:15](=[O:16])[O:14][C@H:13]([C@H:23]2[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH2:24]2)[CH2:12][CH:11]=[CH:10][CH:9]=[C:8]([C:31]#[N:32])[C@H:7]([OH:33])[C@@H:6]([CH3:34])[CH2:5][C@H:4]([CH3:35])[CH2:3]1.[CH:36]1([NH-:42])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 6436801Borrelidin2×

Product 1

HCID 131724641HCID 131724641, compound

Reagents, catalysts & solvents 1

HCID 21584013Chloroform ethylacetateSolvent

Procedure

To a mixed anhydride solution prepared from 200 mg (0.41 mmol) of borrelidin according to Example 3 234 μl (2 mmol, 203 mg) of cyclohexylamine were added. After stirring for 3 hours, the starting borrelidin (Rf=0.52) disappeared and the product (Rf=0.68) appeared, which was proved by thin-layer chromatography (silica gel plate, eluent system: chloroform/ethyl acetate 3:7). The reaction mixture was evaporated to dryness. The dry residue was dissolved in 100 ml of chloroform, washed with 3×30 ml of water, dried over sodium sulfate and evaporated to dryness. The dry residue was chromatographed on a silica gel column with mixtures of chloroform and methanol of increasing methanol content. The fractions containing the product eluting with a 96:4 eluting mixture were combined and evaporated to dryness. The structure of the thus-obtained solidifying oily product (205 mg) was confirmed by spectroscopic (PMR, CMR, TS) data.

Workup

  1. additionwere added
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionThe dry residue was dissolved in 100 ml of chloroform
  4. washwashed with 3×30 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe dry residue was chromatographed on a silica gel column with mixtures of chloroform and methanol of increasing methanol content
  8. additionThe fractions containing the product
  9. washeluting with a 96:4 eluting mixture
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-a68e04d8720244db89ba4139d3de409f
Source dataset
uspto-grants-2004_11
Patent number
US06815465B1

Reaction notes

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