Benzoyl chloride → HCID 59785894, compound

HRID 1673252Notes

Reaction equation

HRID 1673252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C@H:29]([NH2:30])[CH2:28][C:27]([CH3:32])([CH3:31])[O:26][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:16][C:15]=2[Cl:25])=[CH:4][CH:3]=1.CCN(CC)CC.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[OH-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C@H:29]([NH:30][C:40](=[O:47])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH2:28][C:27]([CH3:32])([CH3:31])[O:26][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:16][C:15]=2[Cl:25])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67020004HCID 67020004, compound

Product 1

HCID 59785894HCID 59785894, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step B (35.6 mg, 0.08 mmol) and NEt3 (43 μL, 0.31 mmol) in 10 mL of CH2Cl2 was added benzoyl chloride (20 μL, 0.17 mmol). After stirring at rt for 1 h, 2.0 mL of CH3OH and 100 μL of 5.0 N NaOH was added to the reaction mixture. After stirring for 30 min, the reaction mixture was partitioned between EtOAc (20 mL) and saturated aq NaHCO3 (20 mL). The organic layer was separated and washed with brine (20 mL). After the phases separated, the organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 7:3 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.50 (s, 3H), 1.56 (s, 3H), 1.96 (t, J=12.4, 1H), 2.36 (dd, J=6.4, 13.2, 1H), 5.73 (m, 2H), 6.61 (d, J=8.7, 1H), 7.02 (d, J=8.5, 2H), 7.13 (d, J=8.5, 2H), 7.14-7.55 (m, 6H), 7.72-7.83 (m, 5H).

Workup

  1. stirringAfter stirring for 30 min
  2. customthe reaction mixture was partitioned between EtOAc (20 mL) and saturated aq NaHCO3 (20 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. customAfter the phases separated
  6. dry with materialthe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10eec4006f1843a787c4773b767eb22b
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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