Water → (S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholine-2,3-dione

HRID 16332Notes

Reaction equation

HRID 16332 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].C(Cl)Cl.[Si:10]([O:27][C@H:28]([CH3:44])[C@H:29]([NH:39][CH2:40][C@@H:41]([OH:43])[CH3:42])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Si:10]([O:27][C@H:28]([CH3:44])[C@H:29]([N:39]1[CH2:40][C@H:41]([CH3:42])[O:43][C:2](=[O:3])[C:1]1=[O:5])[C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=1)([C:23]([CH3:25])([CH3:26])[CH3:24])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 68718733(S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol

Product 1

HCID 68718625(S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholine-2,3-dione

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In nitrogen atmosphere, oxalyl chloride (45 μL) was dropwise added to a methylene chloride solution (2 mL) of (S)-1-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propylamino]propan-2-ol (171 mg), TEA (0.17 mL), and 4-(N,N-dimethylamino)pyridine (8 mg) under ice-cooling. This reaction solution was stirred under ice-cooling for 2 hr. To the reaction solution, iced-water and ethyl acetate were added. The organic layer was separated, washed with water, 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. Then, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent; heptane:ethyl acetate=9:1 to 3:1) to give 96 mg of the title compound. The physical property values of this compound were as follows:

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. customThe organic layer was separated
  4. washwashed with water, 1 N hydrochloric acid, water
  5. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent; heptane:ethyl acetate=9:1 to 3:1)

Sources & evidence

ORD record
ord-ccff782b193041dfaeb67fde6cdb7afe
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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