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

HRID 446488Notes

Reaction equation

HRID 446488 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH:13][CH2:14][CH2:15][C:16]1[CH:45]=[CH:44][CH:43]=[CH:42][C:17]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:41][CH2:40][C:24]2([O:29][CH2:28][CH2:27][N:26]([C:30]([C:32]3[N:33]=[C:34]([CH:37]([CH3:39])[CH3:38])[S:35][CH:36]=3)=[O:31])[CH2:25]2)[CH2:23][CH2:22]1.[C:46]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])(=[O:49])[CH:47]=[CH2:48]>C1(C)C=CC=CC=1>[CH:37]([C:34]1[S:35][CH:36]=[C:32]([C:30]([N:26]2[CH2:25][C:24]3([CH2:40][CH2:41][N:21]([CH2:20][CH2:19][O:18][C:17]4[CH:42]=[CH:43][CH:44]=[CH:45][C:16]=4[CH2:15][CH2:14][O:13][CH2:48][CH2:47][C:46]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:22][CH2:23]3)[O:29][CH2:28][CH2:27]2)=[O:31])[N:33]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylate2×HCID 66854Benzyltrimethylammonium hydroxide2×HCID 58168601(9-(2-(2-(2-Hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 58168547Tert-butyl 3-(2-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenethoxy)propanoateYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

benzyltrimethylammonium hydroxide (0.2 mL) was added to (9-(2-(2-(2-hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (0.60 g) (example 178 step b) and tert-butyl acrylate (0.244 g) in toluene (1 mL) and the reaction mixture stirred vigorously. Afire 16 h, more benzyltrimethylammonium hydroxide (0.2 mL) and tert-butyl acrylate (0.244 g) was added. After a further 48 h the reaction mixture was evaporated in vacuo and applied to a silica gel column eluting with 5% methanol in DCM. Yield as a gum 0.52 g.

Workup

  1. customAfter a further 48 h the reaction mixture was evaporated in vacuo
  2. washeluting with 5% methanol in DCM

Sources & evidence

ORD record
ord-2c0804415d0945c4ac21adce73a337d7
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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