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

反応式

HRID 30169 の反応式
[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]

参加物

7

反応物 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)

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-682631f3d77b44cdb9a2a4e47fe13c7b
出典データセット
uspto-grants-2008_09
特許番号
US07423052B2

関連ノート

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