Chloroform → HCID 69652407, compound

HRID 2212212Notes

Reaction equation

HRID 2212212 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH:21]([N:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:33])[C:27]=3[C:26]3=[N:34][O:35][C:36]([CH3:37])=[C:25]3[C:24]2=[O:38])[CH2:20][CH:19]([CH2:39][NH2:40])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCN(CC)CC.C(Cl)(Cl)Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH:21]([N:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:33])[C:27]=3[C:26]3=[N:34][O:35][C:36]([CH3:37])=[C:25]3[C:24]2=[O:38])[CH2:20][CH:19]([CH2:39][NH:40][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 69652392HCID 69652392, compound

Product 1

HCID 69652407HCID 69652407, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add benzoyl chloride (0.11 mL, 0.98 mmol) to a solution of 3-aminomethyl-5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.4 g, 0.89 mmol) in CH2Cl2 (10 mL). Add Et3N (0.4 mL, 2.67 mmol) and DMAP (5 mg, cat.). Stir 4 H at room temperature then add CHCl3. Wash 2× with sat. aq NaHCO3, wash 2× with 1N HCl, wash 2× with brine, dry over Na2SO4, filter and concentrate to dryness. Purify by radial chromatography using a MeOH/CHCl3 gradient as eluant. Purify again via radial chromatography using an EtOAc/hexane gradient as eluant and concentrate to dryness to afford the title compound (0.258 g, 53%) as a white foam as a mixture of cis isomers. MS(IS) 551.3 (M+). Purify via chiral HPLC (Chiralcel OD 4.6×250 mm. Eluant: 35% IPA, 65% heptane. Flow: 1.0 mL/min. UV: 240 nM). Chromatography affords isomer 1 of the title compound (59 mg, 23%) as a white solid. MS(IS) 551.3 (M+); Rt=7.0 min. Chromatography affords isomer 2 of the title compound (124 mg, 48%) as a white solid. MS(IS) 551.3; Rt=15.0 min.

Workup

  1. washWash 2× with sat. aq NaHCO3
  2. washwash 2× with 1N HCl
  3. washwash 2× with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate to dryness
  7. customPurify by radial chromatography
  8. customPurify again via radial chromatography
  9. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-be949cb2696d43b69c26a0673863eee7
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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