tert-Butyl acrylate → tert-Butyl 3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoate

HRID 1255362Notes

Reaction equation

HRID 1255362 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[CH2:7][CH2:8][N:9]1[CH2:12][C:11]2([CH2:17][N:16]([C:18]([C:20]3[N:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[S:23][CH:24]=3)=[O:19])[CH2:15][CH2:14][O:13]2)[CH2:10]1.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[CH:32]=[CH2:33].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(#N)C>[CH:25]([C:22]1[S:23][CH:24]=[C:20]([C:18]([N:16]2[CH2:17][C:11]3([CH2:10][N:9]([CH2:8][CH2:7][C:6]4[CH:5]=[C:4]([CH:30]=[CH:29][CH:28]=4)[CH2:3][CH2:2][O:1][CH2:33][CH2:32][C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:12]3)[O:13][CH2:14][CH2:15]2)=[O:19])[N:21]=1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 58168481(2-(3-(2-Hydroxyethyl)phenethyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 58168616tert-Butyl 3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2-(3-(2-hydroxyethyl)phenethyl)-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(2-isopropylthiazol-4-yl)methanone (475 mg) (example 176 step f) was dissolved in acetonitrile (2 mL) and tert-butyl acrylate (312 mg) was added followed by benzyltrimethylammonium hydroxide (0.15 mL of 40 Wt % aqueous solution). The mixture was stirred at ambient temperature for 3 hours. The volatiles were removed under reduced pressure and the residue purified (silica) eluting with 5% methanol and 1% triethylamine in ethyl acetate to afford the subtitled compound. Yield 460 mg.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue purified (silica)
  3. washeluting with 5% methanol and 1% triethylamine in ethyl acetate

Sources & evidence

ORD record
ord-6dbee2c3f8454f23ae91336fc2483720
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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