Acetonitrile → HCID 58168476, compound

HRID 446471Notes

Reaction equation

HRID 446471 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH:13][CH2:14][CH2:15][C:16]1[S:20][CH:19]=[C:18]([CH2:21][CH2:22][N:23]2[CH2:43][CH2:42][C:26]3([O:31][CH2:30][CH2:29][N:28]([C:32]([C:34]4[N:35]=[C:36]([CH:39]([CH3:41])[CH3:40])[S:37][CH:38]=4)=[O:33])[CH2:27]3)[CH2:25][CH2:24]2)[CH:17]=1.[C:44]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:47])[CH:45]=[CH2:46].C(#N)C>C1(C)C=CC=CC=1>[CH:39]([C:36]1[S:37][CH:38]=[C:34]([C:32]([N:28]2[CH2:27][C:26]3([CH2:42][CH2:43][N:23]([CH2:22][CH2:21][C:18]4[CH:17]=[C:16]([CH2:15][CH2:14][O:13][CH2:46][CH2:45][C:44]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[S:20][CH:19]=4)[CH2:24][CH2:25]3)[O:31][CH2:30][CH2:29]2)=[O:33])[N:35]=1)([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 58168599HCID 58168599, compound

Product 1

HCID 58168476HCID 58168476, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzyltrimethylammonium hydroxide (40% in water, 0.27 mL) was added in one portion to a stirred solution of (9-(2-(5-(2-hydroxyethyl)thiophen-3-yl)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone [Example 78, step b] (0.92 g) and tert-butyl acrylate (0.38 g) in toluene (1 mL). The resultant mixture was stirred vigorously at 20° C. for 4 hours. Acetonitrile (1 mL) was added and the mixture was stirred for 18 hours and then purified without work up. The crude product was purified by flash silica chromatography, using 6% methanol in ethyl acetate with 1% triethylamine as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 0.84 g.

Workup

  1. custompurified without work up
  2. customThe crude product was purified by flash silica chromatography
  3. additionFractions containing the product
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-60631ba96e5d4f28a6096fd22dfc1025
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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