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

HRID 446450Notes

Reaction equation

HRID 446450 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][CH:32]=1)[CH2:7][CH2:8][N:9]1[CH2:29][CH2:28][C:12]2([O:17][CH2:16][CH2:15][N:14]([C:18]([C:20]3[N:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[S:23][CH:24]=3)=[O:19])[CH2:13]2)[CH2:11][CH2:10]1.[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[CH:34]=[CH2:35].[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:14]2[CH2:13][C:12]3([CH2:28][CH2:29][N:9]([CH2:8][CH2:7][C:6]4[CH:5]=[C:4]([CH:32]=[CH:31][CH:30]=4)[CH2:3][CH2:2][O:1][CH2:35][CH2:34][C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:10][CH2:11]3)[O:17][CH2:16][CH2:15]2)=[O:19])[N:21]=1)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 58168488(9-(3-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 58168491tert-Butyl 3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(9-(3-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone [Example 34, step a] (2.4 g) was dissolved in acetonitrile (2 mL) and tert-butyl acrylate (1.7 mL) added, followed by benzyltrimethylammonium hydroxide (40% in water, 0.72 mL). The mixture was stirred at ambient temperature for 3 hours. The volatiles were removed under reduced pressure and the residue purified by flash silica chromatography eluting with 3% methanol in dichloromethane containing 1% ‘880’ aqueous ammonia to afford the subtitled compound Yield 2.7 g.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue purified by flash silica chromatography
  3. washeluting with 3% methanol in dichloromethane containing 1% ‘880’ aqueous ammonia

Sources & evidence

ORD record
ord-069cb865c5ec4a669ddecec236a56252
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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