Water → HCID 57165531, compound

HRID 1489380Notes

Reaction equation

HRID 1489380 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[C@H:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:4]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:14][S:15]([O:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[C@H:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:4]1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56991135HCID 56991135, compound

Product 1

HCID 57165531HCID 57165531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 8.0 g of (3S,5S)-5-hydroxymethyl-3-[(methoxycarbonyl)methyl]-2-pyrrolidinone and 4.95 ml of methanesulphonic acid chloride in 100 ml of methylene chloride, a solution of 9.0 ml of triethylamine in 15 ml of methylene chloride is added dropwise at 0° C. within 15 minutes. The mixture is stirred for one hour at 0° C. and for a further hour at ambient temperature. After the addition of 20 ml of water the organic phase is separated off and washed twice with water. The organic phase is dried over magnesium sulphate and evaporated under reduced pressure in vacuo. The crude product is chromatographed with ethyl acetate/methanol (15:1) over silica gel and the solid obtained is recrystallised from methyl tert.butylether/acetone.

Workup

  1. customis separated off
  2. washwashed twice with water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated under reduced pressure in vacuo
  5. customThe crude product is chromatographed with ethyl acetate/methanol (15:1) over silica gel
  6. customthe solid obtained
  7. customis recrystallised from methyl tert.butylether/acetone

Sources & evidence

ORD record
ord-076b4580780549fa99bc9866ffeca01c
Source dataset
uspto-grants-1997_10
Patent number
US05677466

Reaction notes

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