Methyl 2-(4-bromophenoxy)acetate → (2S,4R)-2-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-2-methyl-propionic acid

HRID 1785926Notes

Reaction equation

HRID 1785926 reaction equation
C[O:2][C:3](=[O:38])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:35](=[O:37])[CH3:36])[CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH:16]([CH3:34])[CH2:15]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].C(N([C@H]1C2C(=CC=CC=2)N(C(=O)C2C=CC(OC)=CC=2)[C@@H](C)C1)C1C=CC(OCC(O)=O)=CC=1)(=O)C.COC(=O)COC1C=CC(Br)=CC=1>>[C:35]([N:13]([C@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C@@H:16]([CH3:34])[CH2:15]1)[C:10]1[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:38])=[O:2])=[CH:8][CH:9]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 700580Methyl 2-(4-bromophenoxy)acetateHCID 58859955(2S,4R)-(4-(Acetyl-[1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenoxy)-acetic acidHCID 689256682-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]amino}-phenyl)-2-methyl-propionic acid methyl ester

Product 1

HCID 58859848(2S,4R)-2-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-2-methyl-propionic acid

Procedure

(2S,4R)-2-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-2-methyl-propionic acid was prepared via saponification of 2-(4-{acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]amino}-phenyl)-2-methyl-propionic acid methyl ester, as described in the synthesis of (2S,4R)-(4-{acetyl-[1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenoxy)-acetic acid. The methyl ester was prepared following general procedure D, substituting 2-(4-bromo-phenyl)-2-methyl-propionic acid for methyl-2-(4-bromophenoxy)-acetate.

Sources & evidence

ORD record
ord-696adee031184bf4b13a8623daac27c8
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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