tert-butyl (S)-3-[(1aR,7bS)-5-fluoro-2-(4-methoxycarbonyl-1,1a,2,7b-tetrahydro-cyclopropa[c]chromen-5-ylsulfamoyl)benzyloxy]pyrrolidine-1-carboxylate → tert-Butyl (R)-3-[(1aR,7bS)-5-fluoro-2-(4-methoxycarbonyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-5-ylsulfamoyl)benzyloxy]pyrrolidine-1-carboxylate

HRID 928072Notes

Reaction equation

HRID 928072 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:22](=[O:40])(=[O:39])[NH:23][C:24]2[CH:25]=[CH:26][C:27]3[C@H:28]4[CH2:38][C@H:29]4[CH2:30][O:31][C:32]=3[C:33]=2[C:34]([O:36][CH3:37])=[O:35])=[C:6]([CH:21]=1)[CH2:7][O:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1.ClS(C1C=CC(F)=CC=1CO[C@@H]1CCN(C(OC(C)(C)C)=O)C1)(=O)=O.NC1C(C(OC)=O)=C2C([C@H]3C[C@H]3CO2)=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:22](=[O:39])(=[O:40])[NH:23][C:24]2[CH:25]=[CH:26][C:27]3[C@H:28]4[CH2:38][C@H:29]4[CH2:30][O:31][C:32]=3[C:33]=2[C:34]([O:36][CH3:37])=[O:35])=[C:6]([CH:21]=1)[CH2:7][O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

Participants

4

Reactant 3

HCID 71007006tert-butyl (S)-3-[(1aR,7bS)-5-fluoro-2-(4-methoxycarbonyl-1,1a,2,7b-tetrahydro-cyclopropa[c]chromen-5-ylsulfamoyl)benzyloxy]pyrrolidine-1-carboxylateHCID 86713369(1AR,7bS)-methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×HCID 86713372tert-butyl (R)-3-(2-chlorosulfonyl-5-fluorobenzyloxy)pyrrolidine-1-carboxylate2×

Product 1

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

Procedure

Prepared by proceeding in a similar manner to Intermediate 214, starting from tert-butyl (R)-3-(2-chlorosulfonyl-5-fluorobenzyloxy)pyrrolidine-1-carboxylate (Intermediate 219) and methyl (1aR,7bS)-5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 42A).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1380ce09368b4aa9ba2bfc4418509e70
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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