Water → HCID 69147906, compound

HRID 747013Notes

Reaction equation

HRID 747013 reaction equation
[OH:1][CH:2]([C:5]1([CH2:19][OH:20])[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6]1)[CH2:3]O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C.O>ClCCl.C([Sn](=O)CCCC)CCC>[OH:1][CH:2]1[C:5]2([CH2:6][N:7]([C:9]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])[CH2:8]2)[CH2:19][O:20][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 69146243Phenylmethyl 3-(1,2-dihydroxyethyl)-3-(hydroxymethyl)-1-azetidinecarboxylate

Product 1

HCID 69147906HCID 69147906, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl 3-(1,2-dihydroxyethyl)-3-(hydroxymethyl)azetidine-1-carboxylate (from step (iii); 956 mg, 3.4 mmol) was dissolved in dichloromethane (150 mL) and dibutyltin oxide (17 mg) was added. p-Toluenesulfonyl chloride (686 mg, 3.6 mmol) was added and the solution was cooled to 0° C. Triethylamine (520 μL, 3.75 mmol) was added dropwise and the solution was then allowed to stir at ambient temperature for 16 hrs. Further triethylamine (260 μL, 1.9 mmol) was added and after stirring for 2 hrs, water (250 mL) was added. The mixture was extracted with dichloromethane (2×250 mL), and the extracts dried (MgSO4) then concentrated. The residue was purified by silica chromatography to give the title compound as an oil (456 mg, 1.7 mmol, 51%).

Workup

  1. stirringafter stirring for 2 hrs
  2. extractionThe mixture was extracted with dichloromethane (2×250 mL)
  3. dry with materialthe extracts dried (MgSO4)
  4. concentrationthen concentrated
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-93889595ed0743a1b4f105213a5b1911
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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