Sodium hydride → HCID 89824458, compound

HRID 879244Notes

Reaction equation

HRID 879244 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:21]([O:25][C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C>[C:21]([O:25][C:26](=[O:35])[C:27]1[CH:28]=[CH:29][C:30]([CH2:33][O:10][CH2:9][C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:31][CH:32]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamateHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 89824458HCID 89824458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

168.5 mg (0.67 mmol) of tert.-butyl-[(2S)-1-hydroxy-3-phenylpropane-2-yl]carbamate were added to 4.9 ml of DMF under argon and mixed with 53.6 mg (1.3 mmol) of sodium hydride (as 60% dispersion in liquid paraffin) at a temperature of 0° C. After 30 minutes 200 mg (0.74 mmol) of tert.-butyl-4-(brommethyl)benzoate was added at a temperature of 0° C. Following completion of measuring, the batch was stirred for 2 hours at RT. Afterwards, the batch was evaporated in the rotation steam boiler, the residue absorbed in ice water and the compound extracted with 50 ml of dichlormethane each. The organic phases were washed in saturated sodium hydride solution, dried over magnesium sulphate and evaporated in a vacuum. The raw product thus obtained is being purified by means of preparative HPLC. 50.2 mg (17% o. th.) of the intermediate of tert.-butyl-4-[({(2S)-2-[(tert.-butoxycarbonyl)amino]-3-phenylpropyl}oxy)methyl]benzoate were obtained.

Workup

  1. customAfterwards, the batch was evaporated in the rotation steam boiler
  2. customthe residue absorbed in ice water
  3. extractionthe compound extracted with 50 ml of dichlormethane each
  4. washThe organic phases were washed in saturated sodium hydride solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in a vacuum
  7. customThe raw product thus obtained
  8. customis being purified by means of preparative HPLC

Sources & evidence

ORD record
ord-9a215f441a664685a7e97f425b7455f9
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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