Isobutyraldehyde → 3-(4-Chloro-phenyl)-3-({4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-isobutyl-amino)-propionic acid

HRID 62643Notes

Reaction equation

HRID 62643 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][CH:6]([NH2:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.[O:16]=[C:17]1[CH2:21][CH2:20][C:19](=[O:22])[N:18]1[CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][C:27]=1[O:34][CH3:35].[CH3:36][CH:37]([CH3:40])[CH:38]=O>>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([N:14]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH2:23][N:18]3[C:17](=[O:16])[CH2:21][CH2:20][C:19]3=[O:22])=[C:27]([O:34][CH3:35])[CH:28]=2)[CH2:36][CH:37]([CH3:40])[CH3:38])[CH2:5][C:4]([OH:3])=[O:15])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 6561IsobutyraldehydeHCID 2847357Ethyl β-amino-4-chlorobenzenepropanoateHCID 896106964-[2-(2,5-Dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzaldehyde

Product 1

HCID 725493473-(4-Chloro-phenyl)-3-({4-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-3-methoxy-benzyl}-isobutyl-amino)-propionic acid

Procedure

Following procedures outlined in Example 1 step 1 is accomplished with 3-Amino-3-(4-chloro-phenyl)-propionic acid ethyl ester (5.2) and Intermediate 4.1 then using 2-methyl-propionaldehyde (3.1) in step 2 after acidic hydrolysis and purification the title compound is isolated as a white foam. Molecular Formula=C27H33ClN2O6; (M+H)+=517; Rt=2.53 min (A), purity 98.8%.

Sources & evidence

ORD record
ord-5db5c89920874f00b6cf57e684b577cb
Source dataset
uspto-grants-2016_09
Patent number
US09447038B2

Reaction notes

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