Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 3-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoylamino}-propionic acid methyl ester

HRID 1095892Notes

Reaction equation

HRID 1095892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]([CH3:25])[C:12]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=1)([OH:17])[C:13]([F:16])([F:15])[F:14])[C:5]([OH:7])=O.Cl.[CH3:27][O:28][C:29](=[O:33])[CH2:30][CH2:31][NH2:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:27][O:28][C:29](=[O:33])[CH2:30][CH2:31][NH:32][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH:11]([CH3:25])[C:12]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=2)([OH:17])[C:13]([F:15])([F:16])[F:14])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 574212683-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid

Product 1

HCID 469399483-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoylamino}-propionic acid methyl ester

Procedure

In analogy to Example 26, step 4, 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-benzoic acid (Example 26, step 3) was reacted with beta-alanin-methyl ester hydrochloride and HBTU at 80° C. 2 h to give the title compound as a colorless viscous oil. MS (m/e, ISP neg. ion)=477.0 [M−H+].

Sources & evidence

ORD record
ord-b92af93ba3e94b1eaa2d5d2c0d5d6697
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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