Pyridine → HCID 57611869, compound

HRID 1919895Notes

Reaction equation

HRID 1919895 reaction equation
[NH2:1][C@H:2]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl>[C:28]([NH:1][C@H:2]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[CH:6][CH:5]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57611910HCID 57611910, compound

Product 1

HCID 57611869HCID 57611869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-[(2S)-2-amino-3-(ethylamino)-3-oxopropyl]benzoate was dissolved in dichloromethane (3.5 mL). Pyridine (0.05 mL) and acetic anhydride (0.05 mL) were added. The reaction was allowed to stir overnight at room temperature under nitrogen. The reaction was transferred to a separatory funnel and washed with saturated sodium bicarbonate. The aqueous layer was extracted three additional times with dichloromethane. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by column chromatography. 1H NMR 600 MHz (CDCl3) δ 7.86 (d, 2H, J=8.4 Hz), 7.23 (d, 2H, J=8.4 Hz), 6.89 (s, 1H), 6.47 (s, 1H), 4.68 (m, 1H), 3.15 (m, 2H), 3.06 (m, 2H), 1.93 (s, 3H), 1.55 (s, 9H), 0.99 (m, 3H). MS: cal'd 335 (MH+), exp 335 (MH+).

Workup

  1. customThe reaction was transferred to a separatory funnel
  2. washwashed with saturated sodium bicarbonate
  3. extractionThe aqueous layer was extracted three additional times with dichloromethane
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was purified by column chromatography

Sources & evidence

ORD record
ord-a9ed6cd3916f4a68b272ed6cb6e1ce32
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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