tert-Butanol → HCID 90052280, compound

HRID 2284742Notes

Reaction equation

HRID 2284742 reaction equation
[C:1]([C:3]([CH2:11][CH2:12][O:13][CH3:14])([CH2:7][CH2:8][O:9][CH3:10])C(O)=O)#[N:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])=CC=1.C([N:34]([CH2:37]C)CC)C.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>O1CCCC1>[C:1]([C:3]([NH:34][C:37](=[O:22])[O:43][C:39]([CH3:42])([CH3:41])[CH3:40])([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][CH2:12][O:13][CH3:14])#[N:2]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 90051767HCID 90051767, compound

Product 1

HCID 90052280HCID 90052280, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-cyano-4-methoxy-2-(2-methoxyethyl)butyric acid (G19, 957 mg) in tetrahydrofuran (8 mL) and tert-butanol (32 mL), diphenylphosphonyl azide (1.63 mL) and triethylamine (1.00 mL) were added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The solvent was evaporated under reduced pressure, and to the obtained residue, ethyl acetate and saturated aqueous sodium chloride were added. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (3-cyano-1,5-dimethoxypentan-3-yl)carbamate (G20, 519 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the obtained residue, ethyl acetate and saturated aqueous sodium chloride were added
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-7d4fc2fa91104b339d3f0a223070ed5b
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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