Benzoyl chloride → HCID 69659657, compound

HRID 722732Notes

Reaction equation

HRID 722732 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:10]2[C:11](=[O:18])[CH:12]([NH2:17])[CH2:13][CH:14]=[CH:15][CH2:16][CH:9]2[CH2:8][CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[N:10]2[C:11](=[O:18])[C@@H:12]([NH:17][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:13][CH:14]=[CH:15][CH2:16][C@H:9]2[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 69659434HCID 69659434, compound

Product 1

HCID 69659657HCID 69659657, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing crude 7-amino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid methyl ester, 42, (50 mg, 0.2 mmol) and Et3N (0.56 mL, 4.0 mmol) in 5 mL THF is treated with excess benzoyl chloride (0.23 mL, 2.0 mmol) and stirred for 5 minutes. The reaction is quenched with MeOH and concentrated. The crude residue obtained is purified by preparative reverse phase HPLC (CH3CN/H2O) to yield 45 mg of desired product. 1H NMR (CDCl3) δ 7.92 (d, J=5.9 Hz, 1H), 7.87 (d, J=7.7 Hz, 2H), 7.57–7.42 (m, 3H), 5.70 (m, 2H), 5.30 (m, 1H), 5.18 (m, 1H), 4.63 (m, 1H), 3.74 (s, 3H), 3.12 (m, 1H), 2.67 (m, 1H), 2.52 (m, 1H), 2.29 (m, 2H), 1.90–1.60 (m, 5H); 13C NMR δ 172.8, 172.3, 166.4, 134.4, 131.8, 129.9, 128.8(2C), 127.3(2C), 125.0, 52.3, 51.8, 51.4, 50.8, 35.4, 34.2, 29.7, 26.4, 15.7.

Workup

  1. customThe reaction is quenched with MeOH
  2. concentrationconcentrated
  3. customThe crude residue obtained
  4. customis purified by preparative reverse phase HPLC (CH3CN/H2O)

Sources & evidence

ORD record
ord-906f3c3861a74ee3b238c5bd4a3aa83f
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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