Hydrochloric Acid → (9-(2-(5-(2-Hydroxyethyl)thiophen-2-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

HRID 470968Notes

Reaction equation

HRID 470968 reaction equation
Cl.[Si]([O:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][CH2:18][N:19]2[CH2:37][CH2:36][C:22]3([O:27][CH2:26][CH2:25][N:24]([C:28]([C:30]4[N:31]=[C:32]([CH3:35])[S:33][CH:34]=4)=[O:29])[CH2:23]3)[CH2:21][CH2:20]2)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C>CO>[OH:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][C:22]3([O:27][CH2:26][CH2:25][N:24]([C:28]([C:30]4[N:31]=[C:32]([CH3:35])[S:33][CH:34]=4)=[O:29])[CH2:23]3)[CH2:36][CH2:37]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57989154(9-(2-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 57988998(9-(2-(5-(2-Hydroxyethyl)thiophen-2-yl)ethyl)-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-(2-(5-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 4, step i) (0.235 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 re-dissolved in methanol (˜2 mL). The residue was dissolved in 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 yellow oil. Yield 0.12 g.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue azeotroped with toluene
  3. dissolutionre-dissolved in methanol (˜2 mL)
  4. dissolutionThe residue was dissolved in 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-1af513c740124034a0029dbd6bc29f10
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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