Potassium Carbonate → HCID 86653083, compound

HRID 2355433Notes

Reaction equation

HRID 2355433 reaction equation
[OH:1][CH2:2][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][NH:5][CH3:6].C([O-])([O-])=O.[K+].[K+].[C:21]([O:30]N1C(=O)CCC1=O)([O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=O>CC(C)=O.O>[C:10]([O:9][C:8]([NH:7][C@H:3]([CH2:4][N:5]([CH3:6])[C:21]([O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])=[O:30])[CH2:2][OH:1])=[O:14])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 57544755Carbamic acid, [(1R)-2-hydroxy-1-[(methylamino)methyl]ethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86653083HCID 86653083, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of crude tert-butyl (R)-3-hydroxy-1-(methylamino)propan-2-ylcarbamate in acetone (30 mL) and water (10 mL), there was added K2CO3 (12.8 g, 92.4 mmol), followed by Teoc-OSu (8.0 g, 30.8 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 (4×15 mL). The combined organic layers were concentrated and the crude residue was purified by flash column chromatography to give (2R)-2-(t-butoxycarbonylamino)-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol (2.12 g, 20% steps). 1H NMR (400 MHz, CDCl3): 5.08 (br, 1H), 4.14 (m, 2H), 3.66-3.42 (m, 4H), 3.02 (m, 1H), 2.90 (s, 3H), 1.40 (S, 9H), 0.98 (m, 2H), 0.02 (s, 9H); MS m/z 349 (M+H+).

Workup

  1. custom(˜1 h)
  2. customAcetone was removed under vacuum
  3. extractionthe aqueous residue was extracted with CH2Cl2 (4×15 mL)
  4. concentrationThe combined organic layers were concentrated
  5. customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-9172614f3d5f4fbba1f826c91b87aa2f
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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