tert-Butyl carbamate → 4-Aminomethyl-N-[4-(4'-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-benzenesulfonamide trifluoroacetate

HRID 1786563Notes

Reaction equation

HRID 1786563 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([C:23](O)=[O:24])[O:20][C:21]=3[CH3:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OC(=O)[NH:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](=[O:43])(=[O:42])[NH2:41])=[CH:36][CH:35]=1)(C)(C)C.C(=O)(OC(C)(C)C)N.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].ClCCl>>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[NH2:32][CH2:33][C:34]1[CH:35]=[CH:36][C:37]([S:40]([NH:41][C:23]([C:19]2[O:20][C:21]([CH3:22])=[C:17]([CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:10][CH:11]=3)[CH:18]=2)=[O:24])(=[O:42])=[O:43])=[CH:38][CH:39]=1

Participants

5

Reactant 4

HCID 77922tert-Butyl carbamateHCID 104272364-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acidHCID 18361086Tert-butyl (4-sulfamoylbenzyl)carbamateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 184446564-Aminomethyl-N-[4-(4'-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-benzenesulfonamide trifluoroacetate

Procedure

4-(4′-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (50 mg) was reacted with (4-sulphamoyl-benzyl)-carbamic acid tert-butyl ester (85 mg) in an analogous manner to that described in Example 2A. The intermediate tert-butyl carbamate was hydrolysed with 1% trifluoroacetic acid/dichloromethane over 24 hours, then concentrated in vacuo to give compound 12 as a white solid (10 mg). LC/MS System C: Rt=4.67 mins, m/z (ES−)=493 (M−1 for C27H26N2O6S).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14da1013d149444fadc18cb28ff0aae9
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

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