3,4,5-Trimethoxybenzoic Acid → HCID 68681847, compound

HRID 1992747Notes

Reaction equation

HRID 1992747 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13]C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[CH:25]=[C:26]([CH3:29])[CH:27]=O.COC1C=C(C=C(OC)C=1OC)C(O)=O.C[N:46](CCCN=C=NCC)C>C(Cl)Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:46][CH2:27][C:26]([CH3:29])=[CH:25][C:19]1[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=1[F:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acidHCID 79330684HCID 79330684, compound

Product 1

HCID 68681847HCID 68681847, compound

Reagents, catalysts & solvents 3

HCID 757711-HydroxybenzotriazoleCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Experimental condition analogous to Example 2 were used with 2-(S)-{[3-(2,4-difluoro-phenyl)-2-methyl-allylaminmo]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester were used with 2-(S)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester and 3-(2,4-difluoro-phenyl)-2-methyl-propenal described in scheme 15) 0.4 g (1 mmol), 3,4,5-trimethoxy benzoic acid 0.27 g (1.3 mmol), triethylamine 0.1 ml, 1-(dimethylaminopropyl)-3-ethylcarbodiimide 0.31 g (1.63 mmol), and 1-hydroxybenzotriazole 0.014 g (0.1 mmol) in 10 ml DCM. The reaction yielded 0.49 g of 2-(S)-{[3-(2,4-difluoro-phenyl)-2-methyl-allylamino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. The compound was transformed to the HCl salt, yielding 45 mg of a white solid. Yield: 14%.

Sources & evidence

ORD record
ord-399dd36180dc4f5c9ed40799c6b13287
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

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