Acrylic Acid → HCID 57595437, compound

HRID 1349574Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:33]([OH:37])(=[O:36])[CH:34]=[CH2:35].ClC1C=CC(N(C(=O)CC)C2C3C(=CC=C(C=CC(O)=O)C=3)N(C(=O)C3C=CC(F)=CC=3)C(C)C2)=CC=1.C(N(C1C=CC(Cl)=CC=1)[C@H]1C2C(=CC=CC=2)N(C(C2C=CC(CCC(O)=O)=CC=2)=O)[C@@H](C)C1)(=O)C>>[C:9]([N:8]([C@H:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:14]([CH3:32])[CH2:13]1)[C:5]1[CH:6]=[CH:7][C:2]([CH2:35][CH2:34][C:33]([OH:37])=[O:36])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

Reactant 4

HCID 6581Acrylic Acid

HCID 58859686HCID 58859686, compound2×

HCID 58860008HCID 58860008, compound

HCID 68921239HCID 68921239, compound

Product 1

HCID 57595437HCID 57595437, compound

Procedure

(2S,4R)-3-(4-{Acetyl-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-amino}-phenyl)-propionic acid was prepared from (2S,4R)-N-(4-bromo-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. (2S,4R)-N-(4-Bromo-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was converted to the acrylic acid using the same procedure described in the synthesis of (±)-3-[4-[(4-chloro-phenyl)-propionyl-amino]-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-6-yl]-acrylic acid. The reduction and saponification were carried out as in the procedure describing the preparation of (2S,4R)-3-(4-{4-[acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-propionic acid.

Sources & evidence

ORD record: ord-43ed4fbc68e94c71adcd76506bcb8a28
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211672B2

Reaction notes

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