3-Hydroxyazetidine → Methyl (1aRS,7bSR)-5-{2-[(Z)-3-(3-hydroxyazetidin-1-yl)prop-1-enyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927963Notes

Reaction equation

HRID 927963 reaction equation
C(NC/C=C\C1C=C(F)C=CC=1S(NC1C(C(OC)=O)=C2C(C3CC3CO2)=CC=1)(=O)=O)C.COC([N:37]([C:52]1[C:61]([C:62]([O:64][CH3:65])=[O:63])=[C:60]2[C:55]([CH:56]3[CH2:66][CH:57]3[CH2:58][O:59]2)=[CH:54][CH:53]=1)[S:38]([C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1/[CH:48]=[CH:49]\[CH2:50]O)(=[O:40])=[O:39])=O.[OH:67][CH:68]1[CH2:71][NH:70][CH2:69]1>>[OH:67][CH:68]1[CH2:71][N:70]([CH2:50]/[CH:49]=[CH:48]\[C:42]2[CH:43]=[C:44]([F:47])[CH:45]=[CH:46][C:41]=2[S:38]([NH:37][C:52]2[C:61]([C:62]([O:64][CH3:65])=[O:63])=[C:60]3[C:55]([CH:56]4[CH2:66][CH:57]4[CH2:58][O:59]3)=[CH:54][CH:53]=2)(=[O:39])=[O:40])[CH2:69]1

Participants

4

Reactant 3

HCID 15142903-HydroxyazetidineHCID 86713248methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylateHCID 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 86713310Methyl (1aRS,7bSR)-5-{2-[(Z)-3-(3-hydroxyazetidin-1-yl)prop-1-enyl]-4-fluorobenzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 63, starting from methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzene-sulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 64) and 3-hydroxyazetidine as a yellow oil.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d9e49dd4eb4141deb2f3e57f44dbaac4
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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