Diisopropylethylamine → (S)-tert-butyl 3,3-dimethyl-2-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butanoate

HRID 923400Notes

Reaction equation

HRID 923400 reaction equation
Cl.[NH2:2][C@@H:3]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:15](=O)([O:24][C@H:25]1[CH2:29][CH2:28][O:27][CH2:26]1)[O:16]N1C(=O)CCC1=O.CCN(C(C)C)C(C)C>C1COCC1>[CH3:12][C:11]([CH3:14])([CH3:13])[C@H:3]([NH:2][C:15]([O:24][C@H:25]1[CH2:29][CH2:28][O:27][CH2:26]1)=[O:16])[C:4]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11229944Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl EsterHCID 56776989tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride

Product 1

HCID 59540266(S)-tert-butyl 3,3-dimethyl-2-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butanoateYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-tert-butyl 2-amino-3,3-dimethylbutanoate hydrochloride (0.05 g, 0.223 mmol), (S)-2,5-dioxopyrrolidin-1-yl tetrahydrofuran-3-yl carbonate (0.056 g, 0.246 mmol) and Hunig's base (0.078 mL, 0.447 mmol) in THF (2.25 mL) was stirred at room temperature for 12 hours. The solvent was evaporated and the product was purified by chromatography on silica gel eluting with 0-15% ethyl acetate in dichloromethane to give the title compound (0.037 g, 55% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified by chromatography on silica gel eluting with 0-15% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-540acb1c069d4c96ba4b0b5d2d885e1a
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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