Tert-Butylamine → 1-t-Butylamino-3-(5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazol-2-yloxy)propan-2-ol

HRID 461688Notes

Reaction equation

HRID 461688 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][CH:16]3[CH:20]4[CH2:21][CH2:22][CH:17]3[CH2:18][CH2:19]4)=[O:12])=[CH:9][N:10]=2)[CH2:2]1.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24]>C(O)C>[C:23]([NH:27][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][CH:16]2[CH:20]3[CH2:21][CH2:22][CH:17]2[CH2:18][CH2:19]3)=[O:12])=[CH:9][N:10]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 213918781,2-Epoxy-3-(5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazol-2-yloxy)propane

Product 1

HCID 213918531-t-Butylamino-3-(5-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazol-2-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-20 °C

Procedure

This example illustrates the second step of the process of the invention for preparing the compounds of formula C. In this example a mixture containing 12 g. (0.037 mole) of 1,2-epoxy-3-[5-(2-(bicyclo[2.2.1]hept-7-yl]ethylaminocarbonyl)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 2 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-[2-(bicyclo[2.2.1]hept-7-yl)ethylaminocarbonyl]thiazol-2-yloxy)propan-2-ol.

Workup

  1. customfor preparing the compounds of formula C
  2. customThe mixture is then evaporated under vacuum
  3. customto remove the ethanol solvent
  4. dissolutionthe resulting residue dissolved in 50 ml
  5. temperaturemaintained at this temperature for 2 hours
  6. filtrationThe mixture is then filtered
  7. filtrationthe resulting filter cake
  8. washwashed with cold (about 0° C) ethyl ether
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1fb64245dadd46ba8564ab578b320ed2
Source dataset
uspto-grants-1977_12
Patent number
US04064135

Reaction notes

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