Hydrochloric Acid → (S)-2-Amino-3-(4-(4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl)phenyl)propanoic acid

HRID 469895Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)#[CH:2].[N:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([NH:30]C(OC(C)(C)C)=O)[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=1)=[N+:17]=[N-:18].Cl>O.O1CCOCC1.CO>[NH2:30][C@@H:26]([CH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH:2]=[C:1]([C:3]3[CH:8]=[CH:7][C:6]([O:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:5][CH:4]=3)[N:18]=[N:17]2)=[CH:20][CH:21]=1)[C:27]([OH:29])=[O:28]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-ethynyl-4-phenoxy-benzene (126 mg, 0.65 mmol) and (S)-3-(4-azido-phenyl)-2-tert-butoxycarbonylamino-propionic acid (200 mg, 0.65 mg) in H2O:dioxane (5:1) was heated at 100° C. in a sealed tube for overnight. After completion of reaction, 3N HCl (5 ml) was added and the mixture was stirred for 2 hr at 50° C. Removal of solvent gave crude product which was dissolved in MeOH and purified by preparative HPLC to give 45 mg of desired product (yield: 29%). 1H-NMR (400 MHz, CD3OD): δ (ppm) 3.2 (m, 1H), 3.4 (m, 1H), 4.3 (m, 1H), 6.9 (d, 2H), 7.0 (d, 2H), 7.2 (m, 1H), 7.3 (d, 2H), 7.4-7.55 (m, 6H), 8.0 (s, 1H).

Workup

additionwas added
customRemoval of solvent
customgave crude product which
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-1d24b3a238e2453094e81a91fb0bca59
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629156B2

Reaction notes

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