Triethylamine → HCID 88630703, compound

HRID 1608368Notes

Reaction equation

[CH3:1][C@@H:2]([NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:3]([O-:5])=[O:4].C(N(CC)CC)C.ClC(OCC)=O.N[CH:28]1[CH:32]([CH3:33])[S:31][S:30][CH:29]1[CH3:34]>O.O1CCCC1>[CH3:34][CH:29]1[CH:28]([N:6]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[C@@H:2]([C:3]([OH:5])=[O:4])[CH3:1])[CH:32]([CH3:33])[S:31][S:30]1

Participants

Conditions

Temperature: -10 °C

Procedure

Under anhydrous conditions, to a mixture of 1.7 g (8.9 mmole) of N-t-Boc-D-alanine obtained in Part A, 1.98 g (19 mmole) triethylamine and 40 ml of tetrahydrofuran, cooled to -10° C. is added dropwise 0.96 g (8.9 mmole) ethyl chloroformate and the resulting mixture is stirred at this temperature for 20 minutes. To this is added 1.1 g (7.5 mmole) of mixed cis- and trans-isomers of 4-amino-3,5-dimethyl-1,2-dithiolane and the resulting mixture is stirred at -10° C. for 10 minutes, then allowed to warm to room temperature. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed with sodium bicarbonate solution, dilute hydrochloric acid, water, brine, then dried (Na2SO4) and the solvent is evaporated at reduced pressure to obtain the desired product which is used in the next step.

Workup

stirringthe resulting mixture is stirred at -10° C. for 10 minutes
temperatureto warm to room temperature
extractionextracted with ethyl acetate
washThe organic layer is washed with sodium bicarbonate solution, dilute hydrochloric acid, water, brine
dry with materialdried (Na2SO4)
customthe solvent is evaporated at reduced pressure

Sources & evidence

ORD record: ord-cbea98f1d6ed436cbd67be34643ce415
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870190

Reaction notes

Loading…