Tetrahydrofuran → HCID 11273779, compound

HRID 2117290Notes

Reaction equation

HRID 2117290 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:17][CH:18]([OH:34])[CH:19]([NH:29][C:30](=[O:33])[CH2:31][NH2:32])[CH2:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1COCC1.[Br:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53](Cl)=[O:54]>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:17][CH:18]([OH:34])[CH:19]([NH:29][C:30](=[O:33])[CH2:31][NH:32][C:53](=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][Br:48])[CH2:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5211735-Bromovaleryl chlorideHCID 11260351HCID 11260351, compound

Product 1

HCID 11273779HCID 11273779, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step 5 (60 mg, 0.12 mmol, 1.00 eq.), triethylamine (33 μL, 0.24 mmol, 2.00 eq.), and anhydrous THF (0.6 mL) is added bromovaleryl chloride (15 μL, 0.11 mmol, 0.95 eq.) under N2 with stirring. The reaction mixture is stirred for 2 hours, then diluted with ethyl acetate, quenched with 1N HCl, and washed with 10% NaHCO3. The organic layer is dried over MgSO4, filtered, and then concentrated in vacuo, yielding product as a white solid (63 mg, 80% crude yield). Calculate mass for C31H43BrFN3O6: 651.23 (mass calculated for Br79 isotope). Mass found for C31H43BrFN3O6: (LCMS) ES+: 676.1 (M+Na), ES− 652.0 (M−1).

Workup

  1. stirringThe reaction mixture is stirred for 2 hours
  2. customquenched with 1N HCl
  3. washwashed with 10% NaHCO3
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf936f89c6c5472da5998ae382d1e704
Source dataset
uspto-grants-2008_10
Patent number
US07442691B2

Reaction notes

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