2-Furancarboxylic acid, hydrazide → (RS)-2-{2-[N'-(1-Furan-2-yl-methanoyl)-hydrazino]-2-oxo-ethyl}-piperidine-1-carboxylic acid tert butyl ester

HRID 549327Notes

Reaction equation

HRID 549327 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[O:51]1[CH:55]=[CH:54][CH:53]=[C:52]1[C:56]([NH:58][NH2:59])=[O:57]>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]([NH:59][NH:58][C:56]([C:52]1[O:51][CH:55]=[CH:54][CH:53]=1)=[O:57])=[O:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 187312-Furancarboxylic acid, hydrazideHCID 81531DiisopropylethylamineHCID 50585361-Boc-2-Piperidineacetic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86629004(RS)-2-{2-[N'-(1-Furan-2-yl-methanoyl)-hydrazino]-2-oxo-ethyl}-piperidine-1-carboxylic acid tert butyl esterYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Carboxymethyl-piperidine-1-carboxylic acid tert butyl ester (2.0 g) was added to [O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate] (3.13 g) in dimethylformamide (10 ml) containing diisopropylethylamine (3.2 g) and the mixture stirred for 15 min. 2-Furoic acid hydrazide (1.04 g) was then added and stirring continued for 16 h. The reaction mixture was diluted with water and extracted with diethyl ether. The combined ether extracts were washed with water, dried and solvent removed at reduced pressure. the residue was column chromatographed (silica gel, 20-50% ethyl acetate/hexane) to give the title compound (2.05 g).

Workup

  1. stirringstirring
  2. waitcontinued for 16 h
  3. extractionextracted with diethyl ether
  4. washThe combined ether extracts were washed with water
  5. customdried
  6. customsolvent removed at reduced pressure
  7. customchromatographed (silica gel, 20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5bd9ca4b85c94bd493c9ed09f7efb7e7
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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