Methylamine → HCID 68281806, compound

HRID 1428966Notes

Reaction equation

HRID 1428966 reaction equation
[CH3:1][NH:2][C:3](C1C=C(B2OC(C)(C)C(C)(C)O2)C=C(C(NC)=O)C=1)=O.[Br:24][C:25]1[CH:26]=[C:27]([C:35]([O:37]C)=O)[CH:28]=[C:29]([CH:34]=1)[C:30](OC)=[O:31].C[NH2:40]>C(O)C>[CH3:1][N:2]([CH3:3])[C:35](=[O:37])[C:27]1[CH:26]=[C:25]([Br:24])[CH:34]=[C:29]([C:30]([NH2:40])=[O:31])[CH:28]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 57413724HCID 57413724, compound

Product 1

HCID 68281806HCID 68281806, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mannosides were synthesized by traditional Lewis acid mediated glycosylation of mannose penta-acetate by reaction with 2-substituted 4-bromophenols using BF3 etherate (Scheme 1). Suzuki cross-coupling with commercially available 3-substituted phenyl boronic acid derivatives gave protected ortho-substituted 4′-biphenyl mannosides in excellent yields and subsequent deprotection with NaOMe gave mannosides 4-5. 6 was prepared following the procedure previously described. Synthesis of di-amides 7-8 followed a similar procedure but required the synthesis of 3,5-di-(N-methyl aminocarbonyl)phenyl boronic acid pinacol ester 9. Shown in Scheme 1, amidation of dimethyl 5-bromoisophthalate by reaction of methylamine in ethanol proceeded in quantitative yield to give N,N-dimethyl 5-bromoisophthalamide. Installation of the boronate ester was accomplished by Pd-mediated coupling with bis(pinacolato)diboron to give 9. Suzuki coupling and deprotection as before yielded compounds 7-8.

Workup

  1. custom6 was prepared

Sources & evidence

ORD record
ord-526d7709dd264f2cb68909a3d8e9c0a4
Source dataset
uspto-grants-2015_01
Patent number
US08937167B2

Reaction notes

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