Potassium Carbonate → (R)-tert-Butyl 2-(6-(1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)hexylthio)ethyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate

HRID 1689464Notes

Reaction equation

HRID 1689464 reaction equation
[OH:1][C@H:2]([C:38]1[C:46]2[S:45][C:44](=[O:47])[NH:43][C:42]=2[C:41]([OH:48])=[CH:40][CH:39]=1)[CH2:3][N:4]([CH2:12][CH2:13][S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:37][CH2:36][C:24]2([O:29][CH2:28][CH2:27][N:26](C(=O)C(F)(F)F)[CH2:25]2)[CH2:23][CH2:22]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+]>CO.O>[O:29]1[C:24]2([CH2:23][CH2:22][N:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][S:14][CH2:13][CH2:12][N:4]([CH2:3][C@H:2]([OH:1])[C:38]3[C:46]4[S:45][C:44](=[O:47])[NH:43][C:42]=4[C:41]([OH:48])=[CH:40][CH:39]=3)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:37][CH2:36]2)[CH2:25][NH:26][CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57989263(R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(2-(6-(4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)hexylthio)ethyl)carbamate

Product 1

HCID 57988895(R)-tert-Butyl 2-(6-(1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)hexylthio)ethyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of (R)-tert-butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(2-(6-(4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)hexylthio)ethyl)carbamate (example 101, step f) (0.18 g) in methanol (10 mL) was added a solution of potassium carbonate (0.06 g) in water (10 mL). The mixture was stirred at RT for 17 h then the methanol was removed under a stream of nitrogen. The solution was diluted with brine, extracted with ethyl acetate (×3) and dried over sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in methanol and evaporated in vacuo to give the subtitled compound as a brown glass. Yield 0.15 g.

Workup

  1. customthe methanol was removed under a stream of nitrogen
  2. additionThe solution was diluted with brine
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in methanol
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-33f257f20dc34a0baf289bf24a9c6657
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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