Methyl Isocyanate → Dihydroqinghaosu Methylcarbamate

HRID 1644

Reaction equation

HRID 1644 reaction equation
[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:19])[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.[CH3:21][N:22]=[C:23]=[O:24]>C(Cl)Cl>[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:19])[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.[CH3:21][NH:22][C:23](=[O:8])[O-:24]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 456410Npc182939

Product 1

HCID 131720552Dihydroqinghaosu MethylcarbamateYield 121.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dihydroqinghaosu (284 mg, 1 mmol) in dry CH2Cl2 (6 ml) and methyl isocyanate (63 mg, 1.1 mmol) was refluxed for ca. 2 days. The solution was filtered and evaporated in vacuo at 40° C. to give a solid, which was chromatographed on a silica-gel column with petroleumether/AcOEt 8:2. The fraction obtained was evaporated to give a white powder (217.6 mg).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated in vacuo at 40° C.
  3. customto give a solid, which
  4. customwas chromatographed on a silica-gel column with petroleumether/AcOEt 8:2
  5. customThe fraction obtained
  6. customwas evaporated

Sources & evidence

ORD record
ord-7d998b7fe2794f36a0da66f08e6c5190
Source dataset
uspto-grants-1998_03
Patent number
US05726203

Linked notes

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