Methanesulfonyl chloride → HCID 10861453, compound

HRID 399514Notes

Reaction equation

HRID 399514 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 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 10861453HCID 10861453, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline tert-butyl ester (573 mg, 1.99 mmol) in pyridine (3.5 mL) cooled to 0° C. was added methanesulfonyl chloride (0.31 mL, 3.99 mmol). The reaction mixture was stirred for 2 hours at ice temperature, diluted with ethyl acetate (30 mL), washed with 1M sodium hydrogencarbonate solution, 1M citric acid, water, dried (Na2SO4), and evaporated. The crude product was purified by flash silica gel chromatography eluting with 1% methanol/dichloromethane; yield 686 mg (94%). 400 MHz 1H NMR (CDCl3): δ1.42-1.44 (2s, 18H); 2.20 (m, 1H); 2.60 (m, 1H); 3.02 (s, 3H); 3.68-3.86 (m, 2H); 4.29 (m, 1H); 5.22 (m, 1H).

Workup

  1. washwashed with 1M sodium hydrogencarbonate solution, 1M citric acid, water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe crude product was purified by flash silica gel chromatography
  5. washeluting with 1% methanol/dichloromethane

Sources & evidence

ORD record
ord-3e7049f39c0d4db8bbce345cdc0ee0e8
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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