Methyl Acetate → (r)-2-(3-{3-[[2,4-Dimethoxybenzyl](2,2-diphenylethyl)amino]-1-methyl-propoxy}-phenyl)acetic acid hydrochloride salt

HRID 229104Notes

Reaction equation

HRID 229104 reaction equation
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][NH:9][CH2:10][CH2:11][C@@H:12]([CH3:24])[O:13][C:14]2[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:31][O:32][C:33]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:34]=1[CH:35]=O.COC(=O)C.[Cl:48]C1C(C(F)(F)F)=CC=CC=1C=O.Cl.CCOCC>CCOCC>[ClH:48].[CH3:31][O:32][C:33]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:34]=1[CH2:35][N:9]([CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:10][CH2:11][C@@H:12]([CH3:24])[O:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 6584Methyl AcetateHCID 691752,4-DimethoxybenzaldehydeHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 10953452Ether hydrochlorideHCID 68864815(R)-2-(3-{3-[(2,2-diphenylethyl)amino]-1-methyl-propoxy}phenyl)acetic acid

Product 1

HCID 68865256(r)-2-(3-{3-[[2,4-Dimethoxybenzyl](2,2-diphenylethyl)amino]-1-methyl-propoxy}-phenyl)acetic acid hydrochloride salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure of Example 7(d) except (R)-2-(3-{3-[(2,2-diphenylethyl)amino]-1-methyl-propoxy}-phenyl)acetic acid and 2,4-dimethoxybenzaldehyde were used instead of (R)-2-(3-{3-(2,2-diphenylethyl)amino]-3-methyl-propoxy}-phenyl)acetic acid methyl ester and 2-chloro-3-trifluoromethylbenzaldehyde in step (d) the corresponding carboxylic acid was obtained. The crude product was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm) to afford the free base. The free base was dissolved in Et2O (diethylether) and acidified with 1.0 M HCl/Et2O. The reaction mixture was concentrated in vacuo and dried under reduced pressure to give the title compound as a white solid, 73 mg (71%). MS (ESI) 554.6 (M+H+).

Workup

  1. customwas obtained
  2. customThe crude product was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm)
  3. customto afford the free base
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-10ff8a1b76b74f3093b24576f64b797a
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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