Potassium bis(trimethylsilyl)amide → HCID 131726814, compound

HRID 898208Notes

Reaction equation

HRID 898208 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[P:11]([O-:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH:32]=[O:33])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH:32]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[OH:33])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 3780918DiethylphosphiteHCID 10398106Benzyl (3-Oxopropyl)carbamate

Product 1

HCID 131726814HCID 131726814, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium bis(trimethylsilyl)amide (1.13 g, 5.66 mmol) in tetrahydrofuran (10 mL) at 0° C. was added diethyl phosphite (0.73 g, 5.66 mmol). After 10 min, 3-(benzyloxycarbonylamino)propanal (0.78 g, 3.77 mmol) was added as a solution in tetrahydrofuran (5 mL). After 30 min, the reaction was quenched by the addition of 2N hydrochloric acid (25 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with sat'd sodium chloride (50 mL), dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with hexane/acetone (1:1) gave a colorless oil (0.36 g): ESI-MS 346.1 (M+H).

Workup

  1. waitAfter 30 min
  2. customthe reaction was quenched by the addition of 2N hydrochloric acid (25 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. washThe organic layer was washed with sat'd sodium chloride (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washSilica gel chromatography eluting with hexane/acetone (1:1)

Sources & evidence

ORD record
ord-97acdf17c27a452e82e8deb88fe8fd98
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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