Triethylamine → HCID 57149177, compound

HRID 2259608Notes

Reaction equation

ClN1C(=O)C[CH2:4][C:3]1=O.C([C:11]1[C:12]([Cl:32])=[C:13](CC)[C:14]([O:24][CH2:25][C:26](=[CH2:29])[CH:27]=[CH2:28])=[C:15]([CH:17]=[N:18][NH:19][P:20](=[O:23])([O-:22])[O-:21])[CH:16]=1)C.[CH2:33](N(CC)CC)[CH3:34]>C(Cl)Cl>[Cl:32][C:12]1[CH:11]=[CH:16][C:15]2[C:17]3[C:26]([CH:27]=[CH2:28])([CH2:25][O:24][C:14]=2[CH:13]=1)[CH2:29][N:19]([P:20](=[O:23])([O:21][CH2:33][CH3:34])[O:22][CH2:3][CH3:4])[N:18]=3

Participants

Conditions

Temperature: 0 °C

Procedure

N-Chlorosuccinimide (1.0 g, 0.007 mol) was added to a mixture of 2.7 g (0.007 mol) of the product from Step D, 0.75 g of 3A molecular sieves and 120 mL of methylene chloride. The resulting mixture was cooled to 0° C. and was treated with a solution of 1.3 mL of triethylamine and 60 mL of methylene chloride. The resulting mixture was stirred at room temperature for 4 h and then decanted into 100 mL of water. The aqueous layer was extracted with two 50 mL portions of methylene chloride and the combined organic layers were washed with water and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated to give 2.9 g of a brown oil. Flash chromatography on silica gel using 1:3 hexanes-EtOAc afforded 1.0 g of a light yellow oil. 200 MHz 1H NMR (CDCl3): δ1.36 (t, 6H), 3.55 (dd, 1H), 3.9 (d, 1H), 4.1-14.3 (m, 5H), 4.60 (d, 1H), 5.15-5.3 (m, 2H), 5.90-6.05 (m, 1H), 6.9-7.0 (m, 2H), 7.78 (d, 1H).

Workup

customdecanted into 100 mL of water
extractionThe aqueous layer was extracted with two 50 mL portions of methylene chloride
washthe combined organic layers were washed with water and saturated sodium bicarbonate solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-51a895594b604e999d7a03c1df71f10d
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05474998

Reaction notes

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