Methanesulfonyl chloride → (4S)-1-(tert-Butyloxycarbonyl)-4-(Methanesulfonyl-oxymethyl)-L-Proline tert-Butyl Ester

HRID 399532Notes

Reaction equation

HRID 399532 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@H:10]([CH2:12][OH:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@H:10]([CH2:12][O:13][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59166759(2S,4S)-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 86753220(4S)-1-(tert-Butyloxycarbonyl)-4-(Methanesulfonyl-oxymethyl)-L-Proline tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S)-1-(tert-butyloxycarbonyl)-4-hydroxymethyl-L-proline tert-butyl ester (364 mg, 1.21 mmol) in pyridine (2 mL) cooled to 0° C. was added methanesulfonyl chloride (0.19 mL, 2.42 mmol). The reaction mixture was stirred for 2 hours at ice temperature, diluted with ethyl acetate (100 mL), washed with 1M sodium hydrogencarbonate solution, 1M citric acid, water, saturated brine solution, dried (Na2 SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 20% acetone/hexane; yield 437 mg (95%).

Workup

  1. washwashed with 1M sodium hydrogencarbonate solution, 1M citric acid, water, saturated brine solution
  2. customdried (Na2 SO4)
  3. customevaporated
  4. customThe crude product was purified by flash silica gel chromatography
  5. washeluting with 20% acetone/hexane

Sources & evidence

ORD record
ord-eb57fdf1d3b44daeb389459cd7761409
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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