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

HRID 16360Notes

Reaction equation

HRID 16360 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 under ice-cooling 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). The resulting reaction solution was stirred at the same temperature for 2 hr, and then iced-water and ethyl acetate were added thereto. The organic layer was separated and 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 (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. customThe resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with water, 1 N hydrochloric acid, water
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=9:1 to 3: 1)

Sources & evidence

ORD record
ord-8588f203c3c2434ca06f9e5bddde947e
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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