HCID 21031126, compound → HCID 22054454, compound

HRID 252189Notes

Reaction equation

HRID 252189 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23](=[O:29])[NH:24][CH2:25][C:26](=[O:28])[NH2:27])=[CH:17][CH:16]=1)C1C=CC=CC=1>CCO.C1COCC1>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([NH:24][CH2:25][C:26](=[O:28])[NH2:27])=[O:29])=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 21031126HCID 21031126, compound

Product 1

HCID 22054454HCID 22054454, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 37 (130 mg, 0.314 mmol) was dissolved in EtOH and THF (14 mL, 1/1 ratio). The reaction vessel was purged with nitrogen both before and after the catalyst (100 mg, 10% Pd/C, 50% wet) was added. The mixture was stirred under hydrogen atmosphere (1 atm) overnight. After purging with nitrogen, the catalyst was vacuum filtered and washed with ethanol (3×5 mL). The combined filtrates were concentrated under vacuum. The residue was chromatographed on silica gel, eluting with a mixture of concentrated ammonium hydroxide/methanol/dichloromethane (2:20:88, v/v), to afford the desired product 38 (80 mg, 91% yield) as a white solid. 1H NMR (300 MHz, CD3OD): δ 1.62 (m, 4H), 2.60 (t, 2H), 2.75 (t, 2H), 3.92 (s, 2H), 4.54 (s, 2H), 6.92 (d, 2H), 7.14 (d, 2H).

Workup

  1. customThe reaction vessel was purged with nitrogen both before and after the catalyst (100 mg, 10% Pd/C, 50% wet)
  2. additionwas added
  3. customAfter purging with nitrogen
  4. filtrationfiltered
  5. washwashed with ethanol (3×5 mL)
  6. concentrationThe combined filtrates were concentrated under vacuum
  7. customThe residue was chromatographed on silica gel
  8. washeluting with a mixture of concentrated ammonium hydroxide/methanol/dichloromethane (2:20:88

Sources & evidence

ORD record
ord-7b893eafac90427db290dbb4850ccde9
Source dataset
uspto-grants-2011_01
Patent number
US07868010B2

Reaction notes

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