Dichloromethane → HCID 57278225, compound

HRID 377076Notes

Reaction equation

HRID 377076 reaction equation
ClCCl.[O:4]1[C@@:21]2([CH3:22])[C@@H:5]1[CH2:6][C@@H:7]1[C:12]([C:13](O)=[O:14])=[CH:11][O:10][C@@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[C@H:8]12.[N-]=[N+]=[N-].C1(OP([O-])(OC2C=CC=CC=2)=O)C=CC=CC=1.Cl.[CH3:44][NH2:45]>ClCCl.CO.C(N(CC)CC)C>[CH3:44][NH:45][C:13]([C:12]1[C@H:7]2[CH2:6][C@@H:5]3[O:4][C@:21]3([CH3:22])[C@@H:8]2[C@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[O:10][CH:11]=1)=[O:14]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6364545Methylamine hydrochlorideHCID 18397301(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acidHCID 21964642Diphenylphosphate azide

Product 1

HCID 57278225HCID 57278225, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A dichloromethane solution containing 395 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid described in Example 1 was cooled with ice followed by addition of 0.49 ml of triethylamine, 0.38 ml of diphenylphosphate azide and 118 mg of methylamine hydrochloride and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain colorless needles from the dichloromethane-methanol eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid methylamide (194 mg, yield: 47%). The physicochemical properties of this compound are described in Table 3, Compound No. 15.

Workup

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-713a7597141f40f58c7ad370f495c26f
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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