Trifluoroacetic acid → HCID 86587867, compound

HRID 2085348Notes

Reaction equation

HRID 2085348 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:31]=[CH:30][C:14]([C:15]([NH:17][C@@H:18]3[CH2:26][C@:21]4([O:25][CH2:24][CH2:23][CH2:22]4)[CH2:20][C@@H:19]3[C:27]([O-:29])=O)=[O:16])=[CH:13][CH:12]=2)=[CH:3][CH2:2]1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33].Cl.[NH2:40][OH:41]>CO.C[O-].[Na+]>[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33].[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:31]=[CH:30][C:14]([C:15]([NH:17][C@@H:18]3[CH2:26][C@:21]4([O:25][CH2:24][CH2:23][CH2:22]4)[CH2:20][C@@H:19]3[C:27]([NH:40][OH:41])=[O:29])=[O:16])=[CH:13][CH:12]=2)=[CH:3][CH2:2]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 443297Hydroxyamine hydrochlorideHCID 86587868HCID 86587868, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 86587867HCID 86587867, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

(5R,7S,8R)-8-{[4-(2H-chromen-4-yl)benzoyl]amino}-1-oxaspiro[4.4]nonane-7-carboxylate from reaction (34e) (0.10 g, 0.23 mmol) was dissolved in a solution of hydroxylamine hydrochloride, methanol and sodium methoxide, (2 mL) under nitrogen atmosphere at room temperature. The reaction was stirred for 1 h, made neutral with TFA, concentrated and purified by HPLC on a C-18 column eluting with an acetonitrile:water:TFA gradient, to give the title compound (0.032 g, 32%) as a white solid. MS found: (M−H)+=433.

Workup

  1. concentrationconcentrated
  2. custompurified by HPLC on a C-18 column
  3. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-2c655aa6bc2245229e587f24e86e3425
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

Loading…