Hexane → HCID 17932014, compound

HRID 2174323Notes

Reaction equation

HRID 2174323 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:16])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[C:22]([CH3:25])([CH3:24])[CH3:23].CN(C)C(=O)C.CCCCCC>C(Cl)(Cl)Cl.C1CCCCC1.B(F)(F)F.CCOCC>[C:22]([O:14][C:13](=[O:15])[CH:12]([Br:16])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])([CH3:25])([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 8058HexaneHCID 31374DimethylacetamideHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492, compound

Product 1

HCID 17932014HCID 17932014, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 8000Boron trifluoride etherateCatalystHCID 6212ChloroformSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of α-bromoglutaric acid-5-benzylester (See Example 18a(i)(a); 1.2 g, 4.0 mmol) in chloroform (Merck, 5 mL) a solution of tert-butyl 2,2,2-trichloroacetimidate (Fluka, 1.57 mL, 8.52 mmol) in cyclohexane (Merck, 5 mL) was added dropwise over 5 minutes. N,N-Dimethylacetamide (Fluka, 0.88 mL) was added followed by boron trifluoride ethyl etherate (Aldrich, 80 μL) as catalyst. The reaction mixture was stirred for 5 days at room temperature. Hexane was added and the organic phase washed with brine three times, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified using normal phase chromatography (Silica column (40 g), solvents: A=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min, flow rate 40 mL/min, UV detection at 214 and 254 nm) affording 1.13 g (79%) of the pure product. Structure was verified by NMR

Workup

  1. washthe organic phase washed with brine three times
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified
  5. waitA=hexane, B=ethyl acetate, gradient: 10 to 35% B over 15 min

Sources & evidence

ORD record
ord-05082266f0714dfaa634dbb968f0fe93
Source dataset
uspto-grants-2015_06
Patent number
US09061080B2

Reaction notes

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