Triethylamine → HCID 86651692, compound

HRID 1255323Notes

Reaction equation

HRID 1255323 reaction equation
Cl.[O:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:20]([C:22]1[N:23]=[C:24]([C:27](O)=[O:28])[S:25][CH:26]=1)[CH3:21].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl.C1COCC1.O>[CH2:20]([C:22]1[N:23]=[C:24]([C:27]([N:5]2[CH2:6][C:7]3([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]3)[O:2][CH2:3][CH2:4]2)=[O:28])[S:25][CH:26]=1)[CH3:21]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 392354584-Ethyl-1,3-thiazole-2-carboxylic acidHCID 66964240Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Product 1

HCID 86651692HCID 86651692, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
16 °C

Procedure

A mixture of tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (limiting reagent), and 4-ethylthiazole-2-carboxylic acid (1 molar equivalent) was suspended in DCM (4.5 volumes) and cooled to 16° C. To this was added triethylamine (5 molar equivalents) in portions. The thick suspension was cooled to 6° C. and T3P (1.1 molar equivalents of a 1.57M in THF) was added drop-wise at 5-15° C. over 0.5 hr. The reaction mixture was allowed to warm to 22° C. and stirred at 22° C. for 2 hr. The mixture was diluted with water (6.5 volumes, 4° C. exotherm) and the mixture was stirred for 10 mins; the aqueous was separated and extracted with DCM (4.5 volumes). The combined organics were washed saturated aq sodium bicarbonate solution (5.5 volumes) and 20% brine solution (1.5 volumes). The organics were dried over anhydrous sodium sulphate, filtered and evaporated to give a brown oil. Yield: 96% of theoretical.

Workup

  1. temperatureThe thick suspension was cooled to 6° C.
  2. temperatureto warm to 22° C.
  3. stirringthe mixture was stirred for 10 mins
  4. customthe aqueous was separated
  5. extractionextracted with DCM (4.5 volumes)
  6. washThe combined organics were washed saturated aq sodium bicarbonate solution (5.5 volumes) and 20% brine solution (1.5 volumes)
  7. dry with materialThe organics were dried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a brown oil

Sources & evidence

ORD record
ord-115491621444452bbdde8ce764cd81fe
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

Loading…