Diisopropylethylamine → HCID 86761809, compound

HRID 1968891Notes

Reaction equation

HRID 1968891 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH2:13][OH:14])[C@H:9]([O:11][CH3:12])[CH3:10])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C>CS(C)=O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH:13]=[O:14])[C@H:9]([O:11][CH3:12])[CH3:10])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 11816842tert-butyl ((2R,3R)-1-hydroxy-3-methoxybutan-2-yl)carbamate

Product 1

HCID 86761809HCID 86761809, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of ((1R,2R)-1-hydroxymethyl-2-methoxy-propyl)-carbamic acid t-butyl ester (5 g, 22 mmol) in DMSO (20 mL) and DCM (250 mL) was added DIEA (12 mL, 69 mmol), followed by dropwise addition of a solution of Py.SO3 (11 g, 69 mmol) in DMSO (50 mL, +20 mL to rinse the funnel). The reaction mixture was stirred at rt for 5 h. After removal of the DCM, the residue was diluted with Et2O (400 mL) and washed with H2O (2×100 mL) and brine (150 mL). The aqueous layer was back extracted with Et2O (100 mL). The combined Et2O layer was washed with saturated NaHCO3 (150 mL) and dried (Na2SO4). The solvent was removed to give the titled compound. MS (MH+ 218).

Workup

  1. washto rinse the funnel)
  2. customAfter removal of the DCM
  3. additionthe residue was diluted with Et2O (400 mL)
  4. washwashed with H2O (2×100 mL) and brine (150 mL)
  5. extractionThe aqueous layer was back extracted with Et2O (100 mL)
  6. washThe combined Et2O layer was washed with saturated NaHCO3 (150 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-5badb49867d94150af90ab312493318f
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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