Diisopropylethylamine → HCID 69679748, compound

HRID 275885Notes

Reaction equation

HRID 275885 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[CH2:28]([O:30][C:31](=[O:46])[CH2:32][CH2:33][NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[CH3:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:28]([O:30][C:31](=[O:46])[CH2:32][CH2:33][N:34]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1)[C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1908440ethyl N-(3,4-dimethoxybenzyl)-beta-alaninateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54466640HCID 54466640, compound

Product 1

HCID 69679748HCID 69679748, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 1. A solution of ({[3-methoxy-4-(3-o-tolylureido)phenyl]-acetyl}-amino)-acetic acid [50 g, Reference Example 3] and 3-(3,4-dimethoxy-benzylamino)-propionic acid ethyl ester [36 g, Reference Example 2(a)] in dimethylformamide (500 ml) was treated with [O-(7-azabenzotriazol-1-yl)-1,1,3,3,-tetramethyluronium hexafluorophosphate] (53.2 g) and diisopropylethylamine (59 ml). After stirring at ambient temperature for 3 hours the reaction mixture was evaporated to dryness and the residue was treated with water (3L). The mixture was extracted twice with ethyl acetate (1L) and then concentrated to dryness. The residue was subjected to flash chromatography on silica eluting initially with ethyl acetate and then with a mixture of ethyl acetate and methanol (9:1, v/v) to give 3-[N-(3,4-dimethoxybenzyl)-2-{2-[3-methoxy-4-(3-o-tolylureido)phenyl]acetylamino}acetamido]propionic acid ethyl ester as a yellow oil (49 g).

Workup

  1. customwas evaporated to dryness
  2. additionthe residue was treated with water (3L)
  3. extractionThe mixture was extracted twice with ethyl acetate (1L)
  4. concentrationconcentrated to dryness
  5. additionwith a mixture of ethyl acetate and methanol (9:1

Sources & evidence

ORD record
ord-29155610a9f4461ea42fbacf1630f6c4
Source dataset
uspto-grants-2002_03
Patent number
US06352977B1

Reaction notes

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