L-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2) → (S)-2-{[(3S,8S)-3-(4-Cyclopentylmethoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid

HRID 391928Notes

Reaction equation

HRID 391928 reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:39][O:38][C:17]4=[CH:18][C:19]5[CH2:20][C@@H:21]([C:35](O)=[O:36])[N:22]([C@H:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH2:27][CH3:28])[CH2:23][C:24]=5[CH:25]=[C:16]4[O:15]3)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.C[O:43][C:44](=[O:62])[C@@H:45]([NH2:61])[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][N:56]=[C:55]([CH3:59])[C:54]=2[CH3:60])=[CH:49][CH:48]=1>>[CH:1]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([C@H:14]3[CH2:39][O:38][C:17]4=[CH:18][C:19]5[CH2:20][C@@H:21]([C:35]([NH:61][C@@H:45]([CH2:46][C:47]6[CH:52]=[CH:51][C:50]([C:53]7[CH:58]=[CH:57][N:56]=[C:55]([CH3:59])[C:54]=7[CH3:60])=[CH:49][CH:48]=6)[C:44]([OH:43])=[O:62])=[O:36])[N:22]([C@H:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH2:27][CH3:28])[CH2:23][C:24]=5[CH:25]=[C:16]4[O:15]3)=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 66719267L-Phenylalanine, 4-(2,3-dimethyl-4-pyridinyl)-, methyl ester, hydrochloride (1:2)HCID 66719277(3S,8S)-3-(4-cyclopentylmethoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid

Product 1

HCID 58327517(S)-2-{[(3S,8S)-3-(4-Cyclopentylmethoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid

Procedure

(3S,8S)-3-(4-Hydroxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl ester (20 mg) was reacted with cyclopentylmethanol according to General Procedure K and the resulting ester was hydrolyzed according to General Procedure AB to provide (3S,8S)-3-(4-cyclopentylmethoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid (18 mg). The title compound (17 mg) was prepared from (3S,8S)-3-(4-cyclopentylmethoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid (18 mg) and (S)-2-amino-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester bis hydrochloride according to General Procedures L and B. LCMS (m/z): 781.

Sources & evidence

ORD record
ord-22e4f27aa3634b0cbe50e2bfb78a482d
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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