Lithium Hydroxide → HCID 131732415, compound

HRID 514607Notes

Reaction equation

HRID 514607 reaction equation
C([O:4][C:5](=[O:38])[C:6]([CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:31])([NH2:29])[CH:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1)(C)C.C(N(C(C1C=CC=CC=1)C)C(=O)C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Li+]>CO.O>[CH2:22]([CH:7]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])=[CH:12][CH:13]=1)[C:6]([CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:31])([NH2:29])[C:5]([OH:38])=[O:4])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 11544195HCID 11544195, compoundHCID 131732416HCID 131732416, compound

Product 1

HCID 131732415HCID 131732415, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the above mixture of crude product 15 and N-benzyl-N-(1-phenyl-ethyl)-benzamide in methanol (30 mL) and water (15 mL) was added lithium hydroxide (831 mg, 34.7 mmol). The resulting suspension was heated to reflux for 48 hours. After cooled downed, the mixture was concentrated to remove methanol. The water layer was taken up with CH2Cl2 (30 mL×3). The organic layer was dried and concentrated. The residue was purified by silica gel column using hexane and ethyl acetate (2:1) as eluent to give 1.406 g white solid, in 85% yield for two steps. 1H NMR (400 MHz, CDCl3): δ7.44 (d, J=8.52 Hz, 2H), 7.37-7.22 (m, 12H), 6.55 (brs, 1H), 4.43 (dd, J1=4.46 Hz, J2=11.32 Hz, 1H), 4.15 (q, J=6.87 Hz, 1H), 3.98 (d, J=13.68 Hz, 1H), 3.64 (d, J=13.68 Hz, 1H), 2.92 (dd, J1=11.34 Hz, J2=16.94 Hz, 1H), 2.41 (dd, J1=4.48 Hz, J2=16.96 Hz, 1H), 1.54 (s, 9H), 1.28 (d, J=6.88 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 174.39, 152.82, 141.25, 138.44, 137.70, 132.56, 129.22, 128.80, 128.62, 128.60, 128.19, 127.81, 127.53, 118.52, 80.86, 57.96, 57.82, 50.61, 36.29, 28.34, 15.68. mp 93-95° C. IR v (Diamond, cm−1): 3307, 1699, 1594, 1081, 698. MS (ESI) m/z found 475.6 (M+H)+.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 48 hours
  3. temperatureAfter cooled downed
  4. concentrationthe mixture was concentrated
  5. customto remove methanol
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-e5d6b60d48aa442582dbf054ecc203fe
Source dataset
uspto-grants-2015_08
Patent number
US09107954B2

Reaction notes

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