Ethylamine → methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate

HRID 927950Notes

Reaction equation

HRID 927950 reaction equation
CS(OS(C)(=O)=O)(=O)=O.COC([N:14]([C:29]1[C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]2[C:32]([CH:33]3[CH2:43][CH:34]3[CH2:35][O:36]2)=[CH:31][CH:30]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1/[CH:25]=[CH:26]\[CH2:27]O)(=[O:17])=[O:16])=O.[CH:44]([N:47](C(C)C)CC)(C)[CH3:45].C(N)C>C(Cl)Cl.O>[CH2:44]([NH:47][CH2:27]/[CH:26]=[CH:25]\[C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[S:15]([NH:14][C:29]1[C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]2[C:32]([CH:33]3[CH2:43][CH:34]3[CH2:35][O:36]2)=[CH:31][CH:30]=1)(=[O:17])=[O:16])[CH3:45]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 86713304methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Product 1

HCID 86713248methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylateYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methane sulfonic anhydride (0.09 g) was added to a stirred, cooled mixture of methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 64, 0.17 g) and N,N-di-isopropyl-N-ethylamine (0.134 g) in DCM (10 mL) at 0° C. The temperature was allowed to rise to room temperature and the mixture was stirred for 2 hours. A solution of ethylamine (2M in toluene, 2 mL) was added and the resultant mixture was stirred at room temperature for 3 hours then diluted with water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (0.09 g) as a white solid.

Workup

  1. temperaturecooled
  2. customto rise to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-4452265775a647a19d57d5930e3510e8
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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