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tert-Butyl acrylate → 2-Methylpentane

HRID 1255316
Notes
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Reaction equation

HRID 1255316 reaction equation
[Cl:1][C:2]1[C:28]([CH2:29][CH2:30][OH:31])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[CH2:24][CH2:23][C:8]2([O:13][CH2:12][CH2:11][N:10]([C:14]([C:16]3[N:17]=[C:18]([CH2:21][CH3:22])[S:19][CH:20]=3)=[O:15])[CH2:9]2)[CH2:7][CH2:6]1.[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[CH:33]=[CH2:34]>O.C(#N)C>[CH3:27][CH2:28][CH2:2][CH:3]([CH3:25])[CH3:4].[Cl:1][C:2]1[C:3]([CH2:4][N:5]2[CH2:6][CH2:7][C:8]3([O:13][CH2:12][CH2:11][N:10]([C:14]([C:16]4[N:17]=[C:18]([CH2:21][CH3:22])[S:19][CH:20]=4)=[O:15])[CH2:9]3)[CH2:23][CH2:24]2)=[CH:25][CH:26]=[CH:27][C:28]=1[CH2:29][CH2:30][O:31][CH2:34][CH2:33][C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 15458tert-Butyl acrylateHCID 58168486(9-(2-Chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-ethylthiazol-4-yl)methanone

Product 2

HCID 78922-MethylpentaneHCID 58168518Tert-butyl 3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

Triton-B (40% in water, 0.94 mL) was added to a solution of (9-(2-chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-ethylthiazol-4-yl)methanone [Example 26, step c] (3.2 g) and tert-butyl acrylate (1.5 mL) in acetonitrile (1 mL) and the resulting mixture stirred overnight at RT. The solvent was evaporated and the residue was purified by flash silica chromatography, elution gradient 1:1:0.05 ethyl acetate:isohexane:triethylamine to 95:5 ethyl acetate:triethylamine to give the subtitled compound as a clear oil. Yield 3.2 g.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash silica chromatography, elution gradient 1:1:0.05 ethyl acetate

Sources & evidence

ORD record
ord-cb42d73e7e4d498a9df220c95d287efb
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455483B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes