3,4,5-Trimethoxybenzoic Acid → HCID 68681644, compound

HRID 1992743Notes

Reaction equation

HRID 1992743 reaction equation
C(OC(N1CCC[C@@H]1C(O)=O)=O)(C)(C)C.COC1C=C(C=C(OC)C=1OC)C(O)=O.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(OC([N:60]1[CH2:64][CH2:63][CH2:62][CH:61]1[CH2:65][CH2:66][N:67]([CH2:82][C:83]([CH3:91])=[CH:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[C:68](=[O:81])[C:69]1[CH:74]=[C:73]([O:75][CH3:76])[C:72]([O:77][CH3:78])=[C:71]([O:79][CH3:80])[CH:70]=1)=O)(C)(C)C>O1CCOCC1.Cl.C(N(CC)CC)C>[CH3:80][O:79][C:71]1[CH:70]=[C:69]([CH:74]=[C:73]([O:75][CH3:76])[C:72]=1[O:77][CH3:78])[C:68]([N:67]([CH2:82][C:83]([CH3:91])=[CH:84][C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)[CH2:66][CH2:65][C@H:61]1[CH2:62][CH2:63][CH2:64][NH:60]1)=[O:81]

Participants

8

Reactant 4

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68683392HCID 68683392, compound

Product 1

HCID 68681644HCID 68681644, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

Experimental condition analogous to Example 13 were used with 2-[2-(2-Methyl-3-phenyl-allylamino)]-ethyl-(R) pyrrolidine-1-carboxylic acid tert-butyl ester (prepared from (R)-Pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester according to the scheme 3) 0.6 g (2 mmol), 3,4,5-trimethoxy benzoic acid 0.51 g (2.4 mmol), O-(benzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate 1.3 g (4 mmol) and triethylamine 0.2 ml. The intermediate 2-{2-[(2-methyl-3-phenyl-allyl)-(3,4,5-trimethoxy-benzoyl)-amino-]-ethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester was dissolved in 10 ml of dioxane and 5 ml of 6 N HCl, yielding 0.35 g of the compound after basic work-up and purification. Yield: 39%.

Sources & evidence

ORD record
ord-849cdbb608a64a96a8cd440a3416ea97
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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