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 1255340Notes

Reaction equation

HRID 1255340 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

To a suspension of (9-(3-(2-hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (limiting reagent) in acetonitrile (5 volumes) was added tert-butyl acrylate (5 molar equivalents) followed by benzyltrimethylammonium hydroxide solution (40% by weight in water, 0.3 molar equivalents). The mixture was stirred at room temperature for 1 hour.

Sources & evidence

ORD record
ord-a34b2f7b205f457bb674ce2d235a1141
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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