Trifluoroacetic acid → HCID 10113901, compound

HRID 2085347Notes

Reaction equation

HRID 2085347 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]2[CH:32]=[CH:31][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](OC)=[O:28])=[O:16])=[CH:13][CH:12]=2)[CH2:3][CH2:2]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].Cl.[NH2:41][OH:42]>CO.C[O-].[Na+]>[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]2[CH:32]=[CH:31][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:41][OH:42])=[O:28])=[O:16])=[CH:13][CH:12]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 443297Hydroxyamine hydrochlorideHCID 86587865HCID 86587865, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 10113901HCID 10113901, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Methyl (5R,7S,8R)-8-{[4-(3,4-dihydro-2H-chromen-4-yl)benzoyl]amino}-1-oxaspiro[4.4]nonane-7-carboxylate from reaction 34f (0.095 g, 0.22 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, 34%) as a white solid. MS found: (M+H)+=435.

Workup

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

Sources & evidence

ORD record
ord-cd02324198014955b9f27ebdbe726765
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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