Trifluoroacetic acid → HCID 86605959, compound

HRID 1434529Notes

Reaction equation

HRID 1434529 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH:13]([N+:15]([O-])=O)[CH2:12][C:11]2=[O:18])[CH:7]=[CH:6][C:5]=1[N:19]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:20]1=[O:26].[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:15][CH:13]1[CH2:14][N:10]([C:8]2[CH:7]=[CH:6][C:5]([N:19]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:20]3=[O:26])=[C:4]([CH3:3])[CH:9]=2)[C:11](=[O:18])[CH2:12]1.[F:30][C:29]([F:32])([F:31])[C:27]([O-:33])=[O:28]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydride3×HCID 86605958HCID 86605958, compound

Product 1

HCID 86605959HCID 86605959, compound

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent2×

Procedure

36 mg (150 μmol) nickel(II)chloride-hexahydrate are dissolved in 2 ml of methanol by treatment with ultrasound and combined with 15 mg (396 μmol) sodium borohydride. 100 mg (300 μmol) of 3-[2-methyl-4-(4-nitro-2-oxo-pyrrolidin-1-yl)-phenyl]-[1,3]-oxazepan-2-one are dissolved in 2 ml of methanol and added in two batches to the reaction solution. After the first quantity has been added a further 21 mg (555 μmol) sodium borohydride are put in. Then the remaining solution of the nitro compound is added in sequence followed by another 21 mg (555 μmol) of sodium borohydride. The mixture is then stirred for five hours at ambient temperature, acidified with TFA and purified by chromatography through reversed phase HPLC.

Workup

  1. additionadded in two batches to the reaction solution
  2. custompurified by chromatography through reversed phase HPLC

Sources & evidence

ORD record
ord-54eb7d0e9bc14b3da9f3d58f1ad80866
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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