Triethylamine → (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

HRID 703582Notes

Reaction equation

HRID 703582 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]([OH:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(O)(=O)C.C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH:24]([O:31][S:40]([CH3:39])(=[O:42])=[O:41])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57248032(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-hydroxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57247090(2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-hydroxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (9.5 g) in acetic acid (150 ml) were added triethylamine (15 ml) and methanesulfonyl chloride (2 ml) at -40° C. and the mixture was stirred at the same temperature for 2 hours under nitrogen atmosphere. Resulting precipitate was filtered off and the filtrate was concentrated in vacuo to give a residue, which was dissolved in a mixture of ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, washed with brine (50 ml) and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-methanesulfonyloxypropyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (3.74 g).

Workup

  1. customResulting precipitate
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a residue, which
  5. customThe organic layer was separated
  6. washwashed with brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent
  9. customgave a residue, which
  10. customwas chromatographed on silica gel (300 ml)
  11. washeluting with a mixture of hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-7a573299e75a4773a44485368b247b2c
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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