Hydrochloric Acid → (2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochloride

HRID 446457Notes

Reaction equation

HRID 446457 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2].[ClH:29]>CC(O)C.CC(OC)(C)C>[ClH:29].[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57989200tert-Butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 66964119(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate in iPrOH (3 volumes) at 40° C. under nitrogen was added a solution of 5-6N HCl in isopropanol (2-2.4 molar equivalents). The mixture was stirred at 40° C. for 18 hours, cooled to room temp and diluted with TBME (4 volumes). Stirred at room temp for 2 hours, collected by filtration, washed with TBME and air dried to leave an off white powder. Yield: 97% of theoretical.

Workup

  1. temperaturecooled to room temp
  2. stirringStirred at room temp for 2 hours
  3. filtrationcollected by filtration
  4. washwashed with TBME and air
  5. customdried
  6. customto leave an off white powder

Sources & evidence

ORD record
ord-8347daa88b0140969db5375dce31758d
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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