Potassium Carbonate → HCID 86626198, compound

HRID 2355484Notes

Reaction equation

HRID 2355484 reaction equation
[CH3:1][O:2][C:3]([CH3:18])([CH3:17])[CH2:4][C@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][NH:7][CH3:8].C([O-])([O-])=O.[K+].[K+].[C:25]([O:34]N1C(=O)CCC1=O)([O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=O>CC(C)=O.O>[CH3:1][O:2][C:3]([CH3:18])([CH3:17])[CH2:4][C@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:6][N:7]([CH3:8])[C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])=[O:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 57544804HCID 57544804, compound

Product 1

HCID 86626198HCID 86626198, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of the above (S)-tert-butyl 4-methoxy-4-methyl-1-(methylamino)pentan-2-ylcarbamate (˜2.99 mmol) in acetone (9 mL) and water (3 mL), there was added K2CO3 (1.24 g, 9.0 mmol), followed by Teoc-OSu (0.85 g, 3.29 mmol). The resulting mixture was stirred at rt until no starting material remained (˜1 h). Acetone was removed under vacuum, and the aqueous residue was extracted with CH2Cl2 (4×5 mL). The combined organic layers were concentrated, and crude residue was purified with flash column chromatography to give (S)-tert-butyl 4-methoxy-4-methyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)pentan-2-ylcarbamate (0.18 g, 15%, 3 steps) as a clear oil. 1H NMR (400 MHz, CDCl3): 4.82, 4.92 (br, 1H), 4.16 (m, 2H), 3.88 (m, 1H), 3.44 (m, 1H), 3.24 (m, 1H), 3.16 (s, 3H), 2.88, 2.90 (s, 3H), 1.44 (s, 9H), 1.18, 1.20 (s, 6H), 0.98 (m, 2H), 0.02 (s, 9H); MS m/z 405 (M+H+).

Workup

  1. custom(˜1 h)
  2. customAcetone was removed under vacuum
  3. extractionthe aqueous residue was extracted with CH2Cl2 (4×5 mL)
  4. concentrationThe combined organic layers were concentrated
  5. customcrude residue was purified with flash column chromatography

Sources & evidence

ORD record
ord-fab1b9969d54485196bdfd1e830e0108
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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