3-Fluoro-p-anisaldehyde → (r)-2-(3-{3-[[3-Fluoro-4-methoxy-benzyl](2,2-diphenylethyl)amino]-2-methyl-propoxy}-phenyl)acetic acid hydrochloride salt

HRID 229103Notes

Reaction equation

HRID 229103 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][C@@H:11]([CH3:24])[CH2:12][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.[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[CH:35]=O.COC(=O)CC1C=CC=C(OCC[C@H](NCC(C2C=CC=CC=2)C2C=CC=CC=2)C)C=1.[Cl:73]C1C(C(F)(F)F)=CC=CC=1C=O.Cl.CCOCC>CCOCC>[ClH:73].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[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][C@@H:11]([CH3:24])[CH2:12][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 676963-Fluoro-p-anisaldehydeHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 10953452Ether hydrochlorideHCID 68862374methyl (R)-2-(3-(3-((2,2-diphenylethyl)amino)butoxy)phenyl)acetateHCID 68862792(R)-2-(3-{3-[(2,2-diphenylethyl)amino]2-methyl-propoxy}phenyl)acetic acid

Product 1

HCID 68861883(r)-2-(3-{3-[[3-Fluoro-4-methoxy-benzyl](2,2-diphenylethyl)amino]-2-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]2-methyl-propoxy}-phenyl)acetic acid (Example 30-Step (a-b)) and 3-fluoro-4-methoxybenzaldehyde 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 resulting amine/carboxylic acid 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, 98 mg (97%). MS (ESI) 542.4 (M+H+).

Workup

  1. customwas obtained
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-6838c99c6939459787ff7675aa95af45
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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