5-(Boc-amino)nicotinic acid → n-butyl(S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetra-hydrofuran-3-carboxylate

HRID 1428218Notes

Reaction equation

HRID 1428218 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([OH:17])=O)[CH:12]=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C@@:19]1([C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH2:23][CH2:22][O:21][CH2:20]1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([NH:18][C@@:19]2([C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH2:23][CH2:22][O:21][CH2:20]2)=[O:17])[CH:12]=[N:13][CH:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 222661545-(Boc-amino)nicotinic acidHCID 59621155Butyl (S)-3-aminotetrahydrofuran-3-carboxylate

Product 1

HCID 68026189n-butyl(S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetra-hydrofuran-3-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 5-tert-butoxycarbonylamino-pyridine-3-carboxylic acid (2.5 mmol) in 20 mL tetrahydrofuran was combined with N,N-carbodiimidazole (2.75 mmol) and stirred for 15 minutes at ambient temperature. Then a solution of n-butyl(S)-3-amino-tetrahydrofuran-3-carboxylate (2.5 mmol) in 4 mL tetrahydrofuran was added and the reaction mixture was stirred further overnight. Then the solvent was distilled off and the crude product thus obtained was purified by chromatography (silica gel; dichloromethane with 1-25% ethanol).

Workup

  1. stirringthe reaction mixture was stirred further overnight
  2. distillationThen the solvent was distilled off

Sources & evidence

ORD record
ord-b566f41cc32140d9aed340fee48923d2
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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