Hydrazine hydrate (1:1) → 2-Furancarboxylic acid, tetrahydro-, hydrazide, (2S)-

HRID 541286Notes

Reaction equation

HRID 541286 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)[N:28]=[N:27]C=2C=1.O.NN>ClCCl>[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([NH:27][NH2:28])=[O:8]

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 446666Tetrahydro-2-furoic acid, (-)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 405663202-Furancarboxylic acid, tetrahydro-, hydrazide, (2S)-Yield 160.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round-bottom flask was added a solution of (S)-tetrahydrofuran-2-carboxylic acid (3.00 g, 25.8 mmol, 1.00 equiv) in dichloromethane (40 mL). EDC.HCl (7.50 g, 39.1 mmol, 1.50 equiv), HOBT (5.20 g, 38.5 mmol, 1.50 equiv), and hydrazine hydrate (2 mL, 2.00 equiv, 99%) were added to the reaction. The resulting solution was stirred overnight at room temperature. The solids were removed by filtration and the filtrate was concentrated in vacuo to furnish 5.38 g (80%) of the title compound as a yellow oil.

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9847b5dc1ffd473aad29b0dad2e9eacf
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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