methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate → Methyl (1aRS,7bSR)-5-(2-{[N-((R)-1-ethylpyrrolidin-3-yl)-N-methyl-carbamoyl]methyl}-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 928007Notes

Reaction equation

HRID 928007 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][C@H:5]([N:8]([CH3:38])[C:9]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[S:19]([NH:22][C:23]2[C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]3[C:26]([CH:27]4[CH2:37][CH:28]4[CH2:29][O:30]3)=[CH:25][CH:24]=2)(=[O:21])=[O:20])=[O:10])[CH2:4]1)[CH3:2].C(CC1C=C(F)C=CC=1S(NC1C(C(OC)=O)=C2C(C3CC3CO2)=CC=1)(=O)=O)(O)=O.Cl.Cl.C(N1CC[C@@H](NC)C1)C>>[CH2:1]([N:3]1[CH2:7][CH2:6][C@@H:5]([N:8]([CH3:38])[C:9]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[S:19]([NH:22][C:23]2[C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]3[C:26]([CH:27]4[CH2:37][CH:28]4[CH2:29][O:30]3)=[CH:25][CH:24]=2)(=[O:21])=[O:20])=[O:10])[CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 71006995methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×HCID 86713257methyl (1aRS,7bSR)-5-(2-{[N-((S)-1-ethylpyrrolidin-3-yl)-N-methylcarbamoyl]-methyl}-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylateHCID 86713336N-((R)-1-ethylpyrrolidin-3-yl)-N-methylamine dihydrochloride2×

Product 1

HCID 86713335Methyl (1aRS,7bSR)-5-(2-{[N-((R)-1-ethylpyrrolidin-3-yl)-N-methyl-carbamoyl]methyl}-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

Procedure

Prepared by proceeding in a similar manner to Intermediate 126, starting from methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 83) and N—((R)-1-ethylpyrrolidin-3-yl)-N-methylamine dihydrochloride (Intermediate 132) as a light brown foam.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ec78972054bf4d7b88c27fcdaa716a33
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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