Potassium Hydroxide → 4-[(tert-Butoxycarbonyl)amino]-4-(carboxymethyl)tetrahydro-2H-pyran, 4-Amino-4-(carboxymethyl)tetrahydro-2H-pyran, N-BOC protected

HRID 1888115Notes

Reaction equation

HRID 1888115 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:15][C:16]([O:18]C)=[O:17])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:15][C:16]([OH:18])=[O:17])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59444264HCID 59444264, compound

Product 1

HCID 170401964-[(tert-Butoxycarbonyl)amino]-4-(carboxymethyl)tetrahydro-2H-pyran, 4-Amino-4-(carboxymethyl)tetrahydro-2H-pyran, N-BOC protectedYield 88.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-yl)acetate (0.73 g, 2.67 mmol) in ethanol (5 mL) and water (2 mL) was added potassium hydroxide (0.3 g, 5.34 mmol) at room temperature. Upon completion of addition, the reaction mixture was heated at 60° C. for 4 hours and then partitioned between ethyl acetate (30 mL) and 1N HCl (10 mL). The ethyl acetate layer was separated, washed with brine (20 mL), dried over sodium sulfate and concentrated to yield the title compound (0.615 g) as a white solid. MS found: (M−H)+=258.2.

Workup

  1. additionUpon completion of addition
  2. custompartitioned between ethyl acetate (30 mL) and 1N HCl (10 mL)
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5bcd81ba766749029da6505bae4b0c31
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

Loading…