Citric Acid → HCID 11959176, compound

HRID 384549Notes

Reaction equation

HRID 384549 reaction equation
C([CH:6]([O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12])[CH2:7][CH2:8][CH3:9])(=O)C(C)C.ClC1[CH:27]=[C:28]([CH:33]=CC=1)[C:29]([O:31]O)=[O:30].C([O-])(O)=O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:29]([O:31][CH:6]([O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)=[O:12])[CH2:7][CH2:8][CH3:9])(=[O:30])[CH:28]([CH3:33])[CH3:27]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate2×HCID 22340961HCID 22340961, compound

Product 1

HCID 11959176HCID 11959176, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (104) (780 mg, 2.3 mmol) in dichloromethane (20 mL) was added m-chloroperoxybenzoic acid (1.03 g, 4.6 mmol) and NaHCO3 (386 mg, 4.6 mmol). After stirring for 16 h at room temperature, another batch of m-chloroperoxybenzoic acid (791 mg, 4.6 mmol) and NaHCO3 (386 mg, 4.6 mmol) was added. The resulting mixture was stirred for another 8 h and then treated with 10% citric acid. After filtration, the organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by reverse phase preparative HPLC to afford 79 mg (11%) of the title compound. 1H NMR (CDCl3, 400 MHz): δ 0.94 (t, J=7.2 Hz, 3H), 1.153 (d, J=7.2 Hz, 3H), 1.150 (d, J=7.2 Hz, 3H), 1.32-1.58 (m, 12H), 1.74 (m, 2H), 2.28 (s, 2H), 2.56 (m, 1H), 3.23 (m, 2H), 5.27 (t, J=6.8 Hz, 1H, NH), 6.71 (t, J=5.6 Hz, 1H). MS (ESI) m/z 358.30 (M+H+).

Workup

  1. stirringThe resulting mixture was stirred for another 8 h
  2. filtrationAfter filtration
  3. customthe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-bdf3052933dd41c9a4cae0ad6c28e737
Source dataset
uspto-grants-2013_02
Patent number
US08367722B2

Reaction notes

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