Water → HCID 59710219, compound

HRID 1191270Notes

Reaction equation

HRID 1191270 reaction equation
[CH3:1][C:2]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:8]1[CH2:19][OH:20])([CH3:4])[CH3:3].[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C.O>C(OCC)(=O)C>[CH3:4][C:2]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C@@H:8]1[CH2:19][O:20][S:24]([CH3:23])(=[O:26])=[O:25])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

Product 1

HCID 59710219HCID 59710219, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl (2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-(hydroxymethyl)-1-pyrrolidinecarboxylate (Registry No. 156129-73-6, 4.0 g) in ethyl acetate (100 mL), methanesulfonyl chloride (1.12 mL) and triethylamine (2.19 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes. The reaction mixture was added by water and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated, obtained the title compound (4.87 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ff4f50aacd0c49b48ec72eedd2944300
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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