Hydrochloric Acid → (9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 1689204Notes

Reaction equation

HRID 1689204 reaction equation
Cl.[Si]([O:9][CH2:10][CH2:11][C:12]1[CH:38]=[CH:37][C:15]([CH2:16][CH2:17][N:18]2[CH2:36][CH2:35][C:21]3([O:26][CH2:25][CH2:24][N:23]([C:27]([C:29]4[N:30]=[C:31]([CH3:34])[S:32][CH:33]=4)=[O:28])[CH2:22]3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C>CO>[OH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH2:17][N:18]2[CH2:36][CH2:35][C:21]3([O:26][CH2:25][CH2:24][N:23]([C:27]([C:29]4[N:30]=[C:31]([CH3:34])[S:32][CH:33]=4)=[O:28])[CH2:22]3)[CH2:20][CH2:19]2)=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57989178(9-(4-(2-(tert-Butyldimethylsilyloxy)ethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 57989159(9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.5 mL) was added to a solution of (9-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 5, step d) (0.3 g) in methanol (5 mL) and the resulting solution stirred for 1 h. The solvent was evaporated in vacuo and the residue azeotroped with toluene and redissolved in methanol (˜2 mL). The residue was diluted with methanol (10 mL) and applied to a SCX cartridge pre-wetted with methanol. The cartridge was washed with methanol (100 mL) and eluted with 1M ammonia in methanol solution (100 mL). The eluent was evaporated in vacuo to give the subtitled compound as a clear oil. Yield 0.2 g.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue azeotroped with toluene
  3. dissolutionredissolved in methanol (˜2 mL)
  4. additionThe residue was diluted with methanol (10 mL)
  5. washThe cartridge was washed with methanol (100 mL)
  6. washeluted with 1M ammonia in methanol solution (100 mL)
  7. customThe eluent was evaporated in vacuo

Sources & evidence

ORD record
ord-00ed91a40e704abfbb71a18fcf20ed3c
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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