Diisopropylethylamine → 3-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester

HRID 1784250Notes

Reaction equation

HRID 1784250 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[CH3:18][O:19][C:20](=[O:31])[C@@H:21]([NH2:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>>[CH3:18][O:19][C:20](=[O:31])[C@@H:21]([NH:30][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[NH:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24720902(S)-Methyl 2-amino-3-(4-bromophenyl)propanoate hydrochlorideHCID 635380315-Chloro-2-(2-methyl-butylamino)-benzoic acid

Product 1

HCID 688628123-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl esterYield 75%

Procedure

As per Procedure A, 5-chloro-2-(2-methyl-butylamino)-benzoic acid (12.44 mmol, 3 g) was treated with (2S)-amino-3-(4-bromo-phenyl)-propionic acid methyl ester hydrochloride (12.44 mmol, 3.66 g), HBTU (14.92 mmol, 5.66 g) and diisopropylethylamine (37.32 mmol, 4.82 g) to yield 3-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester. (4.4 g, 75% yield). LC-MS m/z: 482.8 (M+1)+.

Sources & evidence

ORD record
ord-2c39351245f74f4aae94dd654876cde5
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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