Triethylamine → HCID 10109641, compound

HRID 1072649Notes

Reaction equation

HRID 1072649 reaction equation
Cl.[C:2]([O:6][CH2:7][C@@H:8]([C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]#[N:18])=[O:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].[C:19](=O)([O:27]C1C=CC([N+]([O-])=O)=CC=1)[O:20][CH:21]([O:23][C:24](=[O:26])[CH3:25])[CH3:22].C(N(CC)CC)C>ClCCl>[C:24]([O:23][CH:21]([O:20][C:19]([NH:9][C@H:8]([C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]#[N:18])=[O:11])[CH2:7][O:6][C:2]([CH3:5])([CH3:3])[CH3:4])=[O:27])[CH3:22])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 131725020(2s)-1-(o'-Tert-butylserinyl)pyrrolidine-2-carbonitrile hydrochloride

Product 1

HCID 10109641HCID 10109641, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-1-(O′-tert-butylserinyl)pyrrolidine-2-carbonitrile hydrochloride (30 mg, 0.11 mmol; prepared according to Jenkins et al., WO95/15309), α-acetoxyethyl p-nitrophenyl carbonate (32 mg, 0.12 mmol; prepared according to Alexander et al., J. Med. Chem. 31, 318, 1988) and triethylamine (20 mg, 0.20 mmol) in dichloromethane (25 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.; 4:6) yielding a white solid identified as the title compound (14 mg, 0.038 mmol, 35%).

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.; 4:6)
  6. customyielding a white solid

Sources & evidence

ORD record
ord-808baef0e0a44fc78c934f5e9d8a2d0f
Source dataset
uspto-grants-2005_06
Patent number
US06911467B2

Reaction notes

Loading…