Triethylamine → HCID 86618603, compound

HRID 1436400Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][S:19][C:20]#[N:21])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)C>[CH3:2][O:3][C:4](=[O:9])[CH:5]([NH:6][C:20]1[S:19][CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=2)[N:21]=1)[CH2:7][OH:8]

Participants

Conditions

Temperature: 60 °C

Procedure

Serine methyl ester hydrochloride (1.02 g, 4 mmol) was dissolved in 50 mL of ethanol and 2-(4-bromophenyl)-2-oxoethyl thiocyanate (0.686 g, 4.4 mmol), prepared in step 1 of Example 1, was added followed by triethylamine (0.63 mL, 4.4 mmol). The mixture was heated to 60° C. for 18 h and then cooled and concentrated under reduced pressure. Flash chromatography (1% methanol/chloroform) afforded 1.1 g of 2-[4-(4-bromophenyl)-1,3-thiazol-2-ylamino]-3-hydroxy-propionic acid methyl ester (1.1 g, 79%) as a white solid.

Workup

additionwas added
temperaturecooled
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6f1a959b7f164edeb65cf1857fa638f2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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