Triethylamine → HCID 87425656, compound

HRID 2242182Notes

Reaction equation

HRID 2242182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67506663HCID 67506663, compound

Product 1

HCID 87425656HCID 87425656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Example 17A (19.9 g, 66 mmol) and triethylamine (9.5 mL, 70 mmol) in THF (200 mL) at 0° C. under nitrogen was added methanesulfonyl chloride (15.08 g, 132 mmol) drop wise over 30 minutes. The mixture was allowed to warm up to room temperature, stirred for 12 hours, and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate and the aqueous layer was extracted with ethyl acetate (3×300 mL). The combined organic layers were dried (magnesium sulfate), filtered and concentrated to a yellow oil. The yellow oil was purified using a Biotage 65+ eluting with 100% ethyl acetate to provide the titled compound. MS (ESI) m/e 380 (M+H)+; 1H NMR (300 MHz, CD3OD) δ ppm 1.44 (m, 9 H) 2.22 (m, 1 H) 2.65 (m, 1 H) 3.05 (m, 1 H) 3.14 (d, 3 H) 3.17 (m, 1 H) 3.74 (m, 3.73 Hz, 1 H) 3.81 (m, 2 H) 4.00 (m, 1 H) 4.53 (m, 1 H) 4.70 (m, 2 H) 5.32 (m, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×300 mL)
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customThe yellow oil was purified
  8. wash65+ eluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-faced71852e24a1598ebb3cafca32366
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

Loading…