2-Methyl-2-butene → 2-(1-(Tert-butoxycarbonyl)pyrrolidin-3-yl)thiazole-5-carboxylic acid

HRID 715810Notes

Reaction equation

HRID 715810 reaction equation
[CH:1]([C:3]1[S:7][C:6]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[N:5][CH:4]=1)=[O:2].P([O-])(O)(O)=[O:21].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.C(O)(C)(C)C>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][CH:8]([C:6]2[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][N:5]=2)[CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 105532-Methyl-2-butene2×HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86701991Tert-butyl 3-(5-formylthiazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 867019922-(1-(Tert-butoxycarbonyl)pyrrolidin-3-yl)thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

tert-Butyl 3-(5-formylthiazol-2-yl)pyrrolidine-1-carboxylate (3.65 g, 12.93 mmol) was suspended in water (35 ml) and t-butanol (60 ml). Sodium dihydrogenphosphate (2.094 g, 17.45 mmol) was added, followed by 2-methylbut-2-ene (5.34 ml, 50.4 mmol). After 5 minutes, sodium chlorite (2.92 g, 32.3 mmol) was added in portions over about 5 minutes (mildly exothermic). The reaction was stirred for 1 hour at room temperature, then additional 2-methyl-2-butene (2 mL) was added. After stirring for 2 hours at room temperature, the reaction was concentrated and water (100 mL) was added. The mixture was adjusted to pH 2 by addition of 1N hydrochloric acid, then extracted dichloromethane. The organic extracts were dried over sodium sulfate, filtered and concentrated to provide the title compound.

Workup

  1. stirringAfter stirring for 2 hours at room temperature
  2. concentrationthe reaction was concentrated
  3. additionwater (100 mL) was added
  4. additionThe mixture was adjusted to pH 2 by addition of 1N hydrochloric acid
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9bc93bf6ca3f4132b26d381649aef16b
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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