Triethylamine → HCID 14652550, compound

HRID 2072701Notes

Reaction equation

[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[S:26]1CC(O)S[CH2:28][CH:27]1O.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[NH2:5][C:4]1[S:26][CH:27]=[CH:28][C:3]=1[C:2]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)=[CH:10][CH:11]=1)=[O:1]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1.35 g of the compound prepared in (a) above in 8 ml of dry N,N-dimethylformamide was added, successively and under a nitrogen atmosphere, 0.6 g (4 mmol) of 1,4-dithiane-2,5-diol and 0.14 ml (1 mmol) of triethylamine, and the resultant mixture was heated to 50° C. and maintained at this temperature for 4 hours. After cooling the reaction mixture to 25° C., it was diluted with ethyl acetate and the resultant solution was washed successively with water and a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to yield a crude product which was purified on silica gel employing a mixture of ethyl acetate and hexane in a 1:1 ratio as the eluent to yield a yellow foam.

Workup

additionwas added
temperaturemaintained at this temperature for 4 hours
washthe resultant solution was washed successively with water
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-37212d9b4b544b838641600889150b26
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914096

Reaction notes

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