HCID 21921209, compound → HCID 86592793, compound

HRID 1245112Notes

Reaction equation

ClC1C=CC(N[CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=C(C=1)C(O)=O.[ClH:23].[CH3:24][O:25][C:26](=[O:49])[C@@H:27]([NH2:48])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:31][CH:30]=1>>[CH3:24][O:25][C:26](=[O:49])[CH:27]([NH:48][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:28][C:29]1[C:30]([Cl:23])=[CH:31][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 21921209HCID 21921209, compound

HCID 68869458HCID 68869458, compound

Product 1

HCID 86592793HCID 86592793, compoundYield 92.8%

Procedure

5-Chloro-2-[(napthalen-1-yl-methyl)-amino]-benzoic acid (0.1 g, 0.32 mmol) was treated with (2S)-amino-3-(2′-phenoxy-biphenyl-4-yl)propionic acid methyl ester hydrochloride salt (0.123 g, 0.32 mmol) according to the general procedure A to give 2-{5-Chloro-2-[(naphthalene-1-yl-methyl)-amino]-3-(2′phenoxy-biphenyl-4-yl)-propionic acid methyl ester (0.155 g, 75.6%). This methyl ester (0.15 g, 0.23 mmol) was treated with LiOH (2 eq, 1N aqueous solution) according to the general procedure C to give 2-{5-chloro-2-[(naphthalene-1-yl-methyl)-amino]-3-(2′phenoxy-biphenyl-4-yl)-propionic acid (0.13 g, 90.0%) as white solid. 1HNMR (400 MHz, DMSO-d6): 3.36 (dd, 1H), 3.46 (dd, 1H), 4.79–4.88 (m, 1H), 5.10 (d, 2H), 7.01 (d, 1H), 7.18 (d, 2H), 7.26 (d, 1H), 7.33 (t, 1H), 7.50–7.90 (m, 14H), 7.96 (d, 1H), 8.10–8.20 (m, 1H), 8.22–8.30 (m, 1H), 8.32–8.48 (m, 2H), 9.07 (d, 1H), 13.10 (s, 1H). LC/MS (m/z): 627.2 (M+1)+.

Sources & evidence

ORD record: ord-ea4dfdca8990466b973915c626565763
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122580B2

Reaction notes

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