2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl cis-(3aRS,9bRS)-5-acetyl-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927919Notes

Reaction equation

HRID 927919 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]2[C:16]([C@H:17]3[CH2:29][CH2:28][O:27][C@H:18]3CO2)=[CH:15][CH:14]=1)(=[O:11])=[O:10].[C:30]([N:33]1C2C(=CC=C(N)C=2C(OC)=O)[C@H]2CCO[C@H]2[CH2:34]1)(=[O:32])[CH3:31].BrC1C=C(F)C=CC=1S(Cl)(=O)=O>>[C:30]([N:33]1[C:21]2[C:16](=[CH:15][CH:14]=[C:13]([NH:12][S:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Br:1])(=[O:10])=[O:11])[C:22]=2[C:23]([O:25][CH3:26])=[O:24])[C@H:17]2[CH2:29][CH2:28][O:27][C@H:18]2[CH2:34]1)(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86713280methyl cis-(3aRS,9bRS)-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylateHCID 86713285methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 86713284methyl cis-(3aRS,9bRS)-5-acetyl-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 18, starting from methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (Intermediate 29) and 2-bromo-4-fluorobenzenesulfonyl chloride.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-492f015b859c4736a6a846b132442899
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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