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 30169

Reaction equation

HRID 30169 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 the residue
  7. customchromatographed (silica gel, 20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-682631f3d77b44cdb9a2a4e47fe13c7b
Source dataset
uspto-grants-2008_09
Patent number
US07423052B2

Linked notes

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