Tetrabutylammonium Fluoride → (2-tert-Butylthiazol-4-yl)(9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 471072Notes

Reaction equation

HRID 471072 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][C:29]1[CH:30]=[C:31]([CH2:34][N:35]2[CH2:56][CH2:55][C:38]3([O:43][CH2:42][CH2:41][N:40]([C:44]([C:46]4[N:47]=[C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])[S:49][CH:50]=4)=[O:45])[CH2:39]3)[CH2:37][CH2:36]2)[S:32][CH:33]=1)(C(C)(C)C)(C)C>C1COCC1>[C:51]([C:48]1[S:49][CH:50]=[C:46]([C:44]([N:40]2[CH2:39][C:38]3([CH2:55][CH2:56][N:35]([CH2:34][C:31]4[S:32][CH:33]=[C:29]([CH2:28][CH2:27][OH:26])[CH:30]=4)[CH2:36][CH2:37]3)[O:43][CH2:42][CH2:41]2)=[O:45])[N:47]=1)([CH3:54])([CH3:52])[CH3:53]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57989351(9-((4-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-tert-butylthiazol-4-yl)methanone

Product 1

HCID 57989044(2-tert-Butylthiazol-4-yl)(9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

TBAF (1.5 mL of a 1M solution in THF) was added to stirred solution of (9-((4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-tert-butylthiazol-4-yl)methanone (example 43, step c) (0.300 g) in THF (3 mL). After 1 h the reaction was evaporated to a gum. Purification by silica gel chromatography eluting with ethyl acetate:triethylamine, 20:1 gave the subtitled compound as a gum. Yield 0.22 g.

Workup

  1. customAfter 1 h the reaction was evaporated to a gum
  2. customPurification by silica gel chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ca04178dae5745b8946d58943872f658
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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