Pyridine → HCID 86753842, compound

HRID 1417634Notes

Reaction equation

HRID 1417634 reaction equation
[C:1]([O:5][P:6]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C:28](=O)[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:48][OH:49]>C(O)C>[C:37]([O:36][P:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C:28](=[N:48][OH:49])[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)=[O:7])([CH3:39])([CH3:40])[CH3:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86753843HCID 86753843, compound

Product 1

HCID 86753842HCID 86753842, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound (62) (375 mg, 0.67 mmol) in 10 ml of ethanol was added 1.08 ml (13.4 mmol) of pyridine and 70 mg (1.00 mmol) of hydroxylamine hydrochloride, and the mixture stirred for 7 hours at room temperature. The reaction mixture was concentrated under reduced pressure to a half volume, and ethyl acetate and water were added thereto. After neutralizing with 0.2N HCl, the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 18 g; chloroform:methanol=19: 1) to give 373 mg (97%) of Compound (63).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a half volume, and ethyl acetate and water
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by a silica gel column chromatography (silica gel 18 g; chloroform:methanol=19: 1)

Sources & evidence

ORD record
ord-326727f655114b308b81faf3c787fb6d
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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