Benzyltrimethylammonium hydroxide → tert-Butyl 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoate

HRID 1255300Notes

Reaction equation

HRID 1255300 reaction equation
[OH-:1].[CH2:2]([N+](C)(C)C)[C:3]1[CH:8]=CC=C[CH:4]=1.[OH:13][CH2:14][CH2:15][C:16]1[CH:44]=[CH:43][C:19]([CH2:20][CH2:21][N:22]2[CH2:42][CH2:41][C:25]3([O:30][CH2:29][CH2:28][N:27]([C:31]([C:33]4[N:34]=[C:35]([CH:38]([CH3:40])[CH3:39])[S:36][CH:37]=4)=[O:32])[CH2:26]3)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH:38]([C:35]1[S:36][CH:37]=[C:33]([C:31]([N:27]2[CH2:26][C:25]3([CH2:41][CH2:42][N:22]([CH2:21][CH2:20][C:19]4[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][O:13][CH2:16][CH2:15][C:14]([O:13][C:3]([CH3:2])([CH3:4])[CH3:8])=[O:1])=[CH:44][CH:43]=4)[CH2:23][CH2:24]3)[O:30][CH2:29][CH2:28]2)=[O:32])[N:34]=1)([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 66854Benzyltrimethylammonium hydroxideHCID 58168559(9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 58168551tert-Butyl 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Benzyltrimethylammonium hydroxide (40% in methanol, 0.031 mL) was added to a solution of (9-(4-(2-hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone [Example 1, step c] (0.62 g) in toluene (20 mL). The solvent was removed under reduced pressure and the residue azeotroped with toluene. The resultant liquid, which was just mobile with traces of toluene, was treated dropwise with tert-butyl acrylate (0.225 g). The reaction mixture was stirred at 20° C. for 18 hours. The mixture was purified by flash silica chromatography using 2% methanol in dichloromethane with 1% triethylamine as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 0.550 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped with toluene
  3. additionwas treated dropwise with tert-butyl acrylate (0.225 g)
  4. customThe mixture was purified by flash silica chromatography
  5. additionFractions containing the product
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-256f53835b9b415b895eae76f7dacf0a
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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