Triethylamine → HCID 69076632, compound

HRID 221356Notes

Reaction equation

HRID 221356 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([O:21][CH2:22][C:23]([OH:25])=O)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[CH2:26](OC(Cl)=O)C(C)C.O[NH:35][C:36](=[NH:43])C1C=CN=CC=1>C1(C)C=CC=CC=1>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][CH:18]([O:21][CH2:22][C:23]2[O:25][N:43]=[C:36]([C:6]3[CH:7]=[CH:26][CH:5]=[CH:4][N:3]=3)[N:35]=2)[CH2:19][CH2:20]1)=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 15020822-((1-((Tert-butoxy)carbonyl)piperidin-4-yl)oxy)acetic acidHCID 178513374HCID 178513374, compound

Product 1

HCID 69076632HCID 69076632, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of triethylamine (123 μl, 0.87 mmol) and 4-carboxymethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 1, 227 mg, 0.87 mmol) in toluene (10 ml) was treated with isobutylchloroformate (113 μl, 0.87 mmol). After 20 min, activated powdered 3 Å molecular sieves (0.7 g) and N-hydroxyisonicotinamidine (100 mg, 0.73 mmol) were added and the mixture heated under reflux for 18 h. On cooling, the mixture was filtered through celite, the solvent removed in vacuo and the residue purified by flash chromatography (IH-EtOAc, 7:13) to afford the title compound: RT=3.29 min; m/z (ES+) 361.3 [M+H]+; δH (CDCl3) 1.40 (9H, s), 1.55-1.63 (2H, m), 1.80-1.92 (2H, m), 3.05-3.15 (2H, m), 3.64-3.79 (3H, m), 4.80 (2H, s), 7.90 (2H, d), 8.75 (2H, d).

Workup

  1. additionwere added
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 18 h
  4. temperatureOn cooling
  5. filtrationthe mixture was filtered through celite
  6. customthe solvent removed in vacuo
  7. customthe residue purified by flash chromatography (IH-EtOAc, 7:13)

Sources & evidence

ORD record
ord-1fbb9c42e4514795882c0937239ce94c
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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