Trifluoroacetic acid → HCID 10299722, compound

HRID 2085342Notes

Reaction equation

HRID 2085342 reaction equation
[O:1]=[S:2]1(=[O:34])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]([C:12]2[CH:33]=[CH:32][C:15]([C:16]([NH:18][C@@H:19]3[CH2:27][C@:22]4([O:26][CH2:25][CH2:24][CH2:23]4)[CH2:21][C@@H:20]3[C:28](OC)=[O:29])=[O:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].Cl.[NH2:43][OH:44]>CO.C[O-].[Na+]>[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].[O:34]=[S:2]1(=[O:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]([C:12]2[CH:33]=[CH:32][C:15]([C:16]([NH:18][C@@H:19]3[CH2:27][C@:22]4([O:26][CH2:25][CH2:24][CH2:23]4)[CH2:21][C@@H:20]3[C:28]([NH:43][OH:44])=[O:29])=[O:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 443297Hydroxyamine hydrochlorideHCID 86587864HCID 86587864, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 10299722HCID 10299722, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Methyl (5R,7S,8R)-8-{[4-(1,1-dioxido-3,4-dihydro-2H-1-benzothiopyran-4-yl)benzoyl]amino}-1-oxaspiro[4.4]nonane-7-carboxylate from reaction 33f (0.165 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 (0.03 g, 37%) as a white solid. MS found: (M+H)+=485, (2M+H)+=969.

Workup

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

Sources & evidence

ORD record
ord-f81a0ca685ee451c81363e6240cdefd3
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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