Potassium Carbonate → N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester

HRID 24677Notes

Reaction equation

HRID 24677 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[CH:6]=[C:5]([O:16][CH3:17])[C:4]=1B(O)O.[CH2:21]([O:23][C:24](=[O:45])[C@H:25]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=1)[NH:26][C:27](=[O:36])[C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35])[CH3:22].C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:23][C:24](=[O:45])[C@H:25]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([CH2:9][N:10]3[CH2:15][CH2:14][S:13][CH2:12][CH2:11]3)=[CH:6][C:5]=2[O:16][CH3:17])=[CH:40][CH:39]=1)[NH:26][C:27](=[O:36])[C:28]1[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=1[Cl:34])[CH3:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 225717092,6-Dimethoxy-4-(thiomorpholinomethyl)benzeneboronic acidHCID 54106344(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate

Product 1

HCID 54065008N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl esterYield 15.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dimethoxy-4-(thiomorpholinomethyl)-benzeneboronic acid (1.1 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (0.71 g), Pd(PPh3)4 (1.0 g) and K2CO3 (1.00 g) in DME/H2O (10 mL/0.5 mL) was heated at 80° C. for 6 h under N2. The mixture was worked up and purified according to the procedure described in Example 8-3) to yield 0.15 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(thiomorpholinomethyl)phenyl]-L-phenylalanine ethyl ester. mp. 86-89° C. ESMS: m/z 616 (MH+). HCl salt: mp. 204-205° C.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-f99ab618a70f43b898de3389cea6b161
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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