methyl (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate → Methyl (1aR,7bS)-5-[2-((R)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluoro-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 928071Notes

Reaction equation

[CH2:1]([C@H:3]([O:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C@H:19]3[CH2:29][C@H:20]3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12])[CH3:2].FC1C=CC(S(=O)(=O)NC2C=CC3[C@H]4C[C@H]4COC=3C=2C(OC)=O)=C(C=1)CO[C@@H]1CCN(C(OC(C)(C)C)=O)C1>>[CH2:1]([C@@H:3]([O:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C@H:19]3[CH2:29][C@H:20]3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:12])=[O:13])[CH3:2]

Participants

Reactant 2

HCID 86713274methyl (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HCID 86713371tert-Butyl (R)-3-[(1aR,7bS)-5-fluoro-2-(4-methoxycarbonyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-5-ylsulfamoyl)benzyloxy]pyrrolidine-1-carboxylate2×

Product 1

HCID 86713370Methyl (1aR,7bS)-5-[2-((R)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluoro-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 213, starting from tert-butyl (R)-3-[(1aR,7bS)-5-fluoro-2-(4-methoxycarbonyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-5-ylsulfamoyl)benzyloxy]-pyrrolidine-1-carboxylate (Intermediate 218).

Workup

customPrepared

Sources & evidence

ORD record: ord-0b3af4b835c34f4183e4500bdd13fe94
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290472B2

Reaction notes

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