Hydrochloric Acid → HCID 70359289, compound

HRID 1088962Notes

Reaction equation

HRID 1088962 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@H:19](O)[CH2:18][C@H:17]1[CH2:22][O:23][CH2:24][C:25]([OH:27])=[O:26])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl>O1CCCC1.O>[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@H:19]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][C@H:17]1[CH2:22][O:23][CH2:24][C:25]([OH:27])=[O:26])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67867251HCID 67867251, compound

Product 1

HCID 70359289HCID 70359289, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methanesulfonyl chloride (10 ml) in tetrahydrofuran (20 ml) was dropwise added to a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxymethyloxymethyl-4-hydroxypyrrolidine (19.95 g) and triethylamine (27 ml) in tetrahydrofuran (200 ml) at -10°~-5° C. and the mixture was stirred at the same temperature for 1 hour. The mixture was poured into water (200 ml), adjusted to pH 2.5 with 6N hydrochloric acid and extracted with ethyl acetate (150 ml×2). The organic layer was washed with brine (200 ml×2), dried over magnesium sulfate and concentrated under reduced pressure to give (2S,4R)-1-benzyloxycarbonyl-2-carboxymethyloxymethyl-4-methanesulfonylpyrrolidine (24.85 g).

Workup

  1. extractionextracted with ethyl acetate (150 ml×2)
  2. washThe organic layer was washed with brine (200 ml×2)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bac84a86c56483286d86b6bacf4da9a
Source dataset
uspto-grants-1990_10
Patent number
US04963543

Reaction notes

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