Triphosgene → HCID 68076197, compound

To a mixture of (1S,2S)-2-amino-1-thiazol-2-yl-propan-1-ol and (1R,2S)-2-amino-1-thiazol-2-yl-propan-1-ol (2.9 g, 12.5 mmol) in CH2Cl2 (40 mL) was added under argon NEt3 (10.5 mL, 75 mmol) at 0° C. Then, triphosgene (1.86 g, 6.27 mmol) dissolved in 40 mL of CH2Cl2 was added slowly, and the temperature was allowed to warm from 0° C. to room temperature. The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was then quenched by addition of aqueous NaHCO3. The organic layers were separated, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography using EtOAc in heptane from 0% to 100% in order to give the desired product (330 mg, 13%). LC-MS: [M+H] 185.0; Rt 0.48 min; (LCMS method 1). 1H NMR (400 MHz, CHCl3-d): 7.79 (d, 1H), 7.34 (d, 1H), 5.91 (d, 1H), 5.71 (br s, 1H), 4.48-4.38 (m, 1H), 0.89 (d, 3H).

1. additionwas added under argon NEt3 (10.5 mL, 75 mmol) at 0° C
2. additionwas added slowly
3. temperatureto warm from 0° C. to room temperature
4. customThe reaction mixture was then quenched by addition of aqueous NaHCO3
5. customThe organic layers were separated
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by column chromatography

ORD record

ord-31c0b6a863df4b519276990db5d1acd4

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296733B2