Potassium Carbonate → 3-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester

HRID 1181089Notes

Reaction equation

HRID 1181089 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:19][CH2:20][O:21]S(C1C=CC(C)=CC=1)(=O)=O.[CH3:32][O:33][C:34](=[O:53])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][C:38]=1[CH2:44][CH2:45][NH:46][C:47]([O:49][CH:50]([CH3:52])[CH3:51])=[O:48].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:32][O:33][C:34](=[O:53])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:21][CH2:20][CH2:19][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:39][C:38]=1[CH2:44][CH2:45][NH:46][C:47]([O:49][CH:50]([CH3:51])[CH3:52])=[O:48]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58979267Toluene-4-sulfonic acid 2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethyl esterHCID 589793233-[4-Hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl ester

Product 1

HCID 692310163-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of toluene-4-sulfonic acid 2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethyl ester (44 mg, 0.10 mmol; Preparation 5) and 3-[4-hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl ester (31 mg, 0.10 mmol) in DMF (1.0 mL) was treated with K2CO3 (30 mg). The resulting suspension was stirred at 65° C. for 16 h and diluted with water (10 mL). The mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified using silica gel chromatography (50% EtOAc/hexanes to yield 3-(2-(2-isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-43e99649be8d4fd89f3349f652b1690c
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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