Triethylamine → HCID 131725870, compound

HRID 30090Notes

Reaction equation

HRID 30090 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:4][C@@H:3]([CH2:11][OH:12])[CH2:2]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:12][CH2:11][C@H:3]1[O:4][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[O:1][CH2:2]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69255535HCID 69255535, compound

Product 1

HCID 131725870HCID 131725870, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of intermediate (2-a) (0.023 mol) and triethylamine (0.046 mol) in DCM (40 ml) was stirred at 0° C. A mixture of methanesulfonyl chloride (0.035 mol) in DCM (10 ml) was added dropwise. The mixture was stirred on an ice bath for 2 hours and then washed with H2O/NaCl. The organic layer was dried, filtered and the solvent was evaporated. The residue (oil) was solidified in DIPE. The precipitate was filtered off and dried, yielding 5 g of (S)-2,3-dihydro-1,4-dioxino[2,3-b]pyridine-3-methanol methanesulfonate (ester) (intermediate 3) ([α]D20−27.89°; c=25.10 mg/5 ml in methanol; mp. 136° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred on an ice bath for 2 hours
  3. washwashed with H2O/NaCl
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-64247ffcfed14ada95e9d7a1941a79c3
Source dataset
uspto-grants-2008_09
Patent number
US07423048B2

Reaction notes

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