Tert-Butylamine → HCID 21391926, compound

HRID 461933Notes

Reaction equation

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

Participants

Conditions

Temperature: -20 °C

Procedure

This examole illustrates methods for preparing the compounds of the present invention. In this examole a mixture containing 12 g. (0.037 mole) of 1,2-epoxy-3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane, 12 g. (0.164 mole) of t-butylamine and 20 ml. of ethanol is allowed to stand at room temperature for 12 hours. The mixture is then evaporated under vacuum to remove the ethanol solvent and the resulting residue dissolved in 50 ml. of ethyl acetate and cooled to -20° C, and maintained at this temperature for two hours. The mixture is then filtered and the resulting filter cake washed with cold (about 0° C) ethyl ether and then recrystallized from ethyl acetate affording 1-t-butylamino-3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propan-2-ol, m.p. 140°-148° C.

Workup

customfor preparing the compounds of the present invention
additionIn this examole a mixture containing 12 g
customThe mixture is then evaporated under vacuum
customto remove the ethanol solvent
dissolutionthe resulting residue dissolved in 50 ml
temperaturemaintained at this temperature for two hours
filtrationThe mixture is then filtered
filtrationthe resulting filter cake
washwashed with cold (about 0° C) ethyl ether
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-6f99dc7573184a399922682da6d1ecca
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04064257

Reaction notes

Loading…