Triethylamine → HCID 88630703, compound

HRID 2291518Notes

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-1ec7b07d24d64e15a90a4e13b050b5f2
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797298

Reaction notes

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