Water → HCID 86624150, compound

HRID 602471Notes

Reaction equation

HRID 602471 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][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])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67269775HCID 67269775, compound

Product 1

HCID 86624150HCID 86624150, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of tert-butyl (2R,4R)-2-(3-ethoxy-3-oxopropyl)-4-hydroxypyrrolidine-1-carboxylate (335 mg, 1.2 mmol, step 2 of Example 8) and triethylamine (0.25 mL, 1.8 mmol) in dichloromethane (5 mL) at 0° C. was added methanesulfonyl chloride (0.14 mL, 1.8 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 3 h. To the mixture was added water (10 mL) and extracted with dichloromethane (100 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 462 mg (100%) of the title compound as a yellow oil, which was used for the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef65ecd3c6e34fb4be0ab0e4f1c587b2
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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