Water → HCID 23289981, compound

HRID 366543Notes

Reaction equation

HRID 366543 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:22](=[O:23])[CH:21]2[CH:19]([CH2:20]2)[C:18]1=[O:24].O>ClCCl>[F:7][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:22](=[O:23])[CH:21]2[CH:19]([CH2:20]2)[C:18]1=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 23289979HCID 23289979, compound

Product 1

HCID 23289981HCID 23289981, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfurtrifluoride (76mg) was added dropwise to a stirred solution of 3-(6-hydroxyhex-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione (from step (b), 100mg) in dichloromethane (2.0 ml) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature and water (3 ml) was then added. The reaction mixture was extracted with ether (2×10 ml) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography on silica (5 g) using 40% ethyl acetate/hexane as eluant to give the title compound as a pale yellow oil.

Workup

  1. extractionThe reaction mixture was extracted with ether (2×10 ml)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica (5 g)

Sources & evidence

ORD record
ord-5d2446a9dd504b4ca4e0d60022b3a236
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Reaction notes

Loading…