HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethyl Sulfate → (S)-tert-butyl 2-(methoxy(methyl)amino)-2-oxoethyl(1-methoxybut-3-en-2-yl)carbamate

HRID 627260
Notes
Print preview

Reaction equation

HRID 627260 reaction equation
[OH:1][CH2:2][C@@H:3]([N:6]([CH2:14][C:15]([N:17]([O:19][CH3:20])[CH3:18])=[O:16])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=[CH2:5].S(OC)(O[CH3:25])(=O)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:20][O:19][N:17]([CH3:18])[C:15](=[O:16])[CH2:14][N:6]([C@@H:3]([CH:4]=[CH2:5])[CH2:2][O:1][CH3:25])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 2733832Lithium hexamethyldisilazaneHCID 117940379(S)-tert-butyl 1-hydroxybut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate2×

Product 1

HCID 89863103(S)-tert-butyl 2-(methoxy(methyl)amino)-2-oxoethyl(1-methoxybut-3-en-2-yl)carbamateYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (S)-tert-butyl 1-hydroxybut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 250, 7 g, 24.28 mmol) in THF (75 mL) at 0° C. was added dimethyl sulfate (2.436 mL, 25.49 mmol) followed by LiHMDS (26.7 mL, 26.70 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred for two hours. The reaction mixture was then partitioned between ethyl acetate and water. The layers were separated and the organics were washed with saturated sodium bicarbonate, water and brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (5%-30% ethyl acetate/hexanes) afforded the title compound as a clear oil (6.89 g, 91%).

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. washthe organics were washed with saturated sodium bicarbonate, water and brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-19ab10dddf894b7c911b8f7e6881b933
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309245B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes