Tetrahydrofuran → HCID 59478358, compound

HRID 450765Notes

Reaction equation

HRID 450765 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C1COCC1.[Cl-].[Li+].[BH4-].[Na+]>C(O)C>[CH2:9]([O:8][C:6](=[O:7])[NH:5][C@H:4]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:3][OH:2])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 59479180HCID 59479180, compound

Product 1

HCID 59478358HCID 59478358, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed liquid of 4.40 g of N-[(benzyloxy)carbonyl]-3-[(methylsulfonyl)amino]-D-alanine methyl ester, 100 ml of THF, and 50 ml of ethanol was added 1.13 g of lithium chloride, and 1.01 g of sodium borohydride was further added thereto under ice-cooling. The reaction solution was stirred at room temperature for 14 hours, and the solvent was then evaporated under reduced pressure. After adding 150 ml of water, concentrated hydrochloric acid was added thereto until the pH reached 2 to 3. The solution was extracted with ethyl acetate, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain 3.10 g of benzyl[(1R)-2-hydroxy-1-{[(methylsulfonyl)amino]methyl}ethyl]carbamate as a white solid.

Workup

  1. additionwas further added
  2. temperatureunder ice-cooling
  3. customthe solvent was then evaporated under reduced pressure
  4. additionAfter adding 150 ml of water, concentrated hydrochloric acid
  5. additionwas added
  6. extractionThe solution was extracted with ethyl acetate
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e3a9dc6e2d264146beb72e821a77aa23
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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