Methyl bromoacetate → Methyl alpha-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-primidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate

HRID 380793Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]=[S:24].C(N(CC)C(C)C)(C)C.Cl.[NH2:35][C@H:36]([C:44]([O:46][CH3:47])=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Br[CH2:49][C:50](OC)=[O:51]>O1CCCC1.C(Cl)Cl.C(OCC)C>[CH2:37]([CH:36]([N:35]1[C:50](=[O:51])[CH2:49][S:24][C:23]1=[N:22][C:3]1[CH:4]=[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])[C:6]([F:8])=[CH:7][C:2]=1[Cl:1])[C:44]([O:46][CH3:47])=[O:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl isothiocyanate (0.38 g, 1.0 mmol) and N,N-diisopropylethylamine (1.0 mL) in tetrahydrofuran is treated with L-phenylalanine, methyl ester, hydrochloride (0.18 g, 1.0 mmol), shaken at 40° C. for 1 hour, treated with methyl bromoacetate (0.46 g, 3.0 mmol), shaken at 40° C. for 16 hours, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and 0% to 10% diethyl ether in methylene chloride solutions gives the title product (0.37 g) which is identified by 1H and 13C NMR spectral analyses.

Workup

stirringshaken at 40° C. for 16 hours
concentrationconcentrated in vacuo
customto obtain a residue

Sources & evidence

ORD record: ord-fc90a2e164774f33b6ff891820de9884
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303783B1

Reaction notes

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