Hydrochloric Acid → HCID 11782271, compound

HRID 2054590Notes

Reaction equation

HRID 2054590 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][CH:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>ClCCl>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][CH:7]([O:9][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 121855781-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 11782271HCID 11782271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxy-N-tert-butoxycarbonyl-proline methyl ester (5.89 g, 24 mmol) and triethylamine (4 mL, 28.8 mmol) in dichloromethane (80 mL) was cooled to 0° C. and treated with methylsulfonyl chloride (2.1 mL). After stirring an additional 2 h, the reaction mixture was acidified with 2% HCl (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed successively with sat. aq NaHCO3, and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (5% ethyl acetate in heptane) gave 4-methylsulfonyloxy-N-tert-butoxycarbonyl-proline methyl ester. 1H NMR (CDCl3), 5.25 (m, 1H), 4.41 (m, 1H), 3.78 (m, 5H), 3.06 (s, 3H), 2.61 (m, 1H), 2.22 (m, 1H), 1.46 (s, 9H).

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed successively with sat. aq NaHCO3, and sat. aq NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b72041ab0d454ecbb343a1ec025c4009
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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