2-Fluorobenzenesulphonyl chloride → methyl (1aRS,7bSR)-5-(2-Fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927955Notes

Reaction equation

HRID 927955 reaction equation
BrC1C=C(F)C=CC=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([CH:17]3[CH2:27][CH:18]3[CH2:19][O:20]2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].NC1C(C(OC)=O)=C2C(C3CC3CO2)=CC=1.[F:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1S(Cl)(=O)=O>>[F:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([CH:17]3[CH2:27][CH:18]3[CH2:19][O:20]2)=[CH:15][CH:14]=1)(=[O:10])=[O:11]

Participants

4

Reactant 3

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 86713292methyl (1aRS,7bSR)-5-(2-bromo-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylateHCID 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Product 1

HCID 71006854methyl (1aRS,7bSR)-5-(2-Fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 41, starting from methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 42) and 2-fluorobenzenesulfonyl chloride.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-328c46db5814463ba23e6a1ea9b5bc41
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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