Methanesulfonyl chloride → HCID 71740081, compound

HRID 399526Notes

Reaction equation

HRID 399526 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@H:10]([O:12][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67640213HCID 67640213, compound

Product 1

HCID 71740081HCID 71740081, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline tert-butyl ester (313 mg, 1.09 mmol) in pyridine (2.0 mL) cooled to 0° C. was added methanesulfonyl chloride (0.17 mL, 2.18 mmol). The reaction mixture was allowed to reach room temperature, and after 2 hours was diluted with ethyl acetate (100 mL), washed with saturated sodium hydrogencarbonate solution, 1 M citric acid, water, dried (Na2 SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 15% acetone/hexane; yield 251 mg (52% over 2 steps). 400 MHz 1H NMR (CDCl3): δ1.42-1.48 (3s, 18H); 2.38-2.50 (m, 2H); 2.99 (2s, 3H); 3.69-3.79 (m, 2H); 5.22 (m, 1H).

Workup

  1. customto reach room temperature
  2. washwashed with saturated sodium hydrogencarbonate solution, 1 M citric acid, water
  3. customdried (Na2 SO4)
  4. customevaporated
  5. customThe crude product was purified by flash silica gel chromatography
  6. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-c1b7daaa9b774acdad1df8e361aa4967
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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