Hydroxyamine hydrochloride → HCID 9887810, compound

HRID 1872211Notes

Reaction equation

HRID 1872211 reaction equation
[CH2:1]([C@H:8]([NH:16][C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=2)=[O:18])[C:9]([N:11]1[CH2:14][C:13](=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:29].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:38]O>CO>[CH2:1]([C@H:8]([NH:16][C:17]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=2)=[O:18])[C:9]([N:11]1[CH2:12][C:13](=[N:38][OH:29])[CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 57254829HCID 57254829, compound

Product 1

HCID 9887810HCID 9887810, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-chloro-1H-indole-2-carboxylic acid [(1S)-benzyl-2-(3-oxo-azetidin-1-yl)-2-oxo-ethyl]-amide (product of Example 170, 50 mg, 0.13 mmol), sodium acetate trihydrate (43 mg, 0.32 mmol) and hydroxylamine hydrochloride (18 mg, 0.25 mmol) in methanol (2 mL) was heated at reflux for 8 h and concentrated. The residue was partitioned between dichloromethane and saturated aqueous NaHCO3. The organic layer was separated and dried giving a colorless solid which was triturated with ether-hexanes and dried (yield 36 mg, 69%): HPLC (50/50) 6.74 min (99%); TSPMS 411/413 (MH+, 10%), 180 (100%); 1H NMR (DMSO-d6) δ 11.75 (br, 1H), 11.10 (s, 0.5H), 11.08 (s, 0.5H), 8.99 (d, 1H, J=9 Hz), 7.73 (d, 1H, J=2 Hz), 7.4-7.1 (m, 8H), 5.0 (m, 1H), 4.84.5 (m, 4H), 3.1 (m, 2H).

Workup

  1. temperatureat reflux for 8 h
  2. concentrationconcentrated
  3. customThe residue was partitioned between dichloromethane and saturated aqueous NaHCO3
  4. customThe organic layer was separated
  5. customdried
  6. customgiving a colorless solid which
  7. customwas triturated with ether-hexanes
  8. customdried (yield 36 mg, 69%)
  9. customHPLC (50/50) 6.74 min (99%)

Sources & evidence

ORD record
ord-83d957e1b51a4eb880c496d348590bde
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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