methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate → (2S)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid

HRID 1869813Notes

Reaction equation

HRID 1869813 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[C:4]([NH:6][C@H:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:8]([OH:10])=[O:9])=[O:5].C(OC(N[C@H](CC1C=C2C(=CC=1)NC(C1C(Cl)=CC=CC=1Cl)CC2SC1C=CC=CC=1)C(OC)=O)=O)(C)(C)C.C(OC(N[C@H](CC1C=C2C(=CC=1)N=C(C1C(Cl)=CC=CC=1Cl)C=C2)C(OC)=O)=O)(C)(C)C.N[C@H](CC1C=C2C(=CC=1)N=C(C1C(Cl)=CC=CC=1Cl)C=C2)C(OC)=O>>[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:8]([OH:10])=[O:9])=[O:5]

Participants

5

Reactant 4

HCID 11351984methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoateHCID 11467397methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-4-(phenylsulfanyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoateHCID 44429938(2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acidHCID 86619056methyl (2R)-2-amino-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate

Product 1

HCID 9958757(2S)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid

Procedure

(2R)-2-[(2,6-dichlorobenzoyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoic acid 40 can be synthesised according to the same procedure but starting from (D)-p-nitro-Phe-OMe, involving methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-4-(phenylsulfanyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoate 25a, methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 26a and methyl (2R)-2-amino-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 34a (MS (MH+): 375/377/379) as intermediates.

Sources & evidence

ORD record
ord-7281db29ff684f0a82da5717bf9da75b
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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