Triethylamine → HCID 69517592, compound

HRID 1375738Notes

Reaction equation

HRID 1375738 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]#[N:16])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5].[C:17](=O)([O:25]C1C=CC([N+]([O-])=O)=CC=1)[O:18][CH:19]([O:21][C:22](=[O:24])[CH3:23])[CH3:20].C(N(CC)CC)C>ClCCl>[C:22]([O:21][CH:19]([O:18][C:17]([NH:2][C@H:3]([C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]#[N:16])=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5])=[O:25])[CH3:20])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 69520335HCID 69520335, compound

Product 1

HCID 69517592HCID 69517592, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-1-(isoleucyl)pyrrolidine-2-carbonitrile hydrochloride (500 mg, 2.04 mmol; prepared according to Jenkins et al., WO95/15309), α-acetoxyethyl p-nitrophenyl carbonate (610 mg, 2.27 mmol; prepared according to Alexander et al., J. Med. Chem. 31, 318, 1988) and triethylamine (250 mg, 2.50 mmol) in dichloromethane (40 ml) was stirred at room temperature for 18 hours. After this time the solvent was removed in vacuo and the residue was taken up in ethyl acetate (70 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (eluant EtOAc:Pet. Ether 60–80° C.; 3:7) yielding a colourless oil identified as the title compound (480 mg, 1.42 mmol, 70%).

Workup

  1. customAfter this time the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography (eluant EtOAc:Pet. Ether 60–80° C.; 3:7)
  6. customyielding a colourless oil

Sources & evidence

ORD record
ord-48766d505c0c4e0192d6e0bffb4bd9c8
Source dataset
uspto-grants-2007_01
Patent number
US07169806B2

Reaction notes

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