Hydrochloric Acid → methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 928060Notes

Reaction equation

HRID 928060 reaction equation
Cl.[Si]([O:9][CH2:10]/[C:11](/[CH3:43])=[CH:12]\[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[S:20]([N:23]([C:28]1[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:36]2[C:31]([CH:32]3[CH2:42][CH:33]3[CH2:34][O:35]2)=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21])(C(C)(C)C)(C)C>CO>[F:19][C:17]1[CH:16]=[CH:15][C:14]([S:20]([N:23]([C:28]2[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:36]3[C:31]([CH:32]4[CH2:42][CH:33]4[CH2:34][O:35]3)=[CH:30][CH:29]=2)[C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21])=[C:13](/[CH:12]=[C:11](/[CH3:43])\[CH2:10][OH:9])[CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86713360methyl (1aRS,7bSR)-5-(N-{2-[(Z)-3-(tert-butyldimethylsilanyloxy)-2-methylprop-1-enyl]-4-fluorobenzenesulfonyl]-N-methoxycarbonyl-amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Product 1

HCID 71007016methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (1 mL) was added to a solution of methyl (1aRS,7bSR)-5-(N-{2[(Z)-3-(tert-butyldimethylsilanyloxy)-2-methylprop-1-enyl]-4-fluorobenzenesulfonyl]-N-methoxycarbonyl-amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 202, 0.385 g) in methanol (20 mL) and the mixture was left at room temperature for 45 minutes. The solution was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.314 g) as a white foam.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

Sources & evidence

ORD record
ord-b86f538c27c645b4858d5a001299372f
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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