Trimethylsilyl iodide → Rel-n-(2-{[(3r,4r)-4-(allyloxy)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 564399Notes

Reaction equation

[CH2:1]([O:4][C@H:5]1[C@H:9]([NH:10][C:11](=[O:26])[CH2:12][NH:13][C:14](=[O:25])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[CH2:6]1)[CH:2]=[CH2:3].[Si](I)(C)(C)C>C(#N)C>[CH2:1]([O:4][C@@H:5]1[CH2:6][NH:7][CH2:8][C@H:9]1[NH:10][C:11](=[O:26])[CH2:12][NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=1)[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of benzyl rel-(3R,4R)-3-(allyloxy)-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidine-1-carboxylate (575.6 mg, 1.13 mmol) in acetonitrile (5 mL) at 0° C. was added TMSI (1.3 mL, 9.04 mmol) dropwise. The reaction mixture was stirred at 0° C. for 2 h and room temperature for 3 h. The reaction was quenched by adding HCl (1N, 15 mL). The mixture was extracted from with EtOAc (15 mL×3). The aqueous phase was neutralized with NaOH (1N) to pH=10. DCM/isopropanol (4:1, 10 mL×3) was used to extract from the aqueous layer. The organic layers then were combined, dried over MgSO4, filtered, concentrated under reduced pressure to afford rel-N-(2-{[(3R,4R)-4-(allyloxy)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide which was used without further purification (115.6 mg).

Workup

customThe reaction was quenched
additionby adding HCl (1N, 15 mL)
extractionThe mixture was extracted from with EtOAc (15 mL×3)
extractionto extract from the aqueous layer
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ece7cae7471d4c249f638489f743873b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067457B2

Reaction notes

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