Ethanol → HCID 23122072, compound

HRID 1457548Notes

Reaction equation

HRID 1457548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:27][CH2:28]CN=C=NCC.C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1.C(O)C>C(Cl)Cl>[CH2:27]([O:22][C:21]([CH:9]1[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:23])[CH3:28]

Participants

7

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acid

Product 1

HCID 23122072HCID 23122072, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N,N'-di-tert-butyloxycarbonylpiperazine-2-carboxylic acid (4.6 g, 0.013 mol), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (3.2 g, 0.016 mol), triethylamine (2.2 mL, 0.016 mol) and 4-pyrrolidinopyridine (0.23 g, 1.5 mmol) in CH2Cl2 (120 mL) was added ethanol (0.93 mL, 0.016 mol). The mixture was left stirring overnight, then the mixture was washed with water (2×50 mL), 5% aqueous acetic acid (2×300 mL) and water (2×50 mL). The organic phase was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (1:1) to give the ester (3.3 g, 72%) as a colourless oil. 1H NMR (360 MHz, CDCl3) δ 1.28 (3H, t, J=7.1 Hz), 1.44 (9H, s), 2.70-3.32 (3H, m), 3.70-4.12 (2H, m), 4.14-4.26 (2H, m), 4.46-4.76 (2H, m). MS (ES+) 359 (M+1).

Workup

  1. waitThe mixture was left
  2. washthe mixture was washed with water (2×50 mL), 5% aqueous acetic acid (2×300 mL) and water (2×50 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with petrol:EtOAc (1:1)

Sources & evidence

ORD record
ord-bd82adff59ec4971bb15d1537026d3b5
Source dataset
uspto-grants-1998_12
Patent number
US05849746

Reaction notes

Loading…