Methyl 3-aminopropanoate hydrochloride → (+/-)-3-({4-Chloro-5-[1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester

HRID 661005Notes

Reaction equation

HRID 661005 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.CO[C:22]([C:24]1[S:25][C:26]([CH:30](O)[CH2:31][CH3:32])=[C:27]([Cl:29])[CH:28]=1)=[O:23].Cl.[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH2:40]>>[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH:40][C:22]([C:24]1[S:25][C:26]([CH:30]([O:8][C:6]2[CH:5]=[C:4]([CH3:9])[C:3]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[CH:12][CH:11]=3)=[C:2]([CH3:1])[CH:7]=2)[CH2:31][CH3:32])=[C:27]([Cl:29])[CH:28]=1)=[O:23]

Participants

4

Reactant 3

HCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 593559694-Chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 59356035(+/-)-3-({4-Chloro-5-[1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester

Procedure

This compound is made by the general method as exemplified in Preparation 94 using 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol and 4-chloro-5-(1-hydroxy-propyl)-thiophene-2-carboxylic acid methyl ester in Step A and 3-amino-propionic acid methyl ester hydrochloride salt in Step C as the starting materials to provide (±)-3-({4-chloro-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (0.094 g) as a white foam. MS (ES): 552.2 [M−H]−.

Sources & evidence

ORD record
ord-91193e15e3c14466b17e3ffbed2e578e
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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