Triethylamine → HCID 9967171, compound

HRID 1375742Notes

Reaction equation

HRID 1375742 reaction equation
FC(F)(F)C(O)=O.[C:8]([S:12][CH2:13][C@@H:14]([C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]#[N:24])=[O:17])[NH2:15])([CH3:11])([CH3:10])[CH3:9].[CH2:25]([O:27][C:28](Cl)=[O:29])[CH3:26].C(N(CC)CC)C>ClCCl>[C:8]([S:12][CH2:13][C@@H:14]([C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]#[N:24])=[O:17])[NH:15][C:28]([O:27][CH2:25][CH3:26])=[O:29])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 20806679HCID 20806679, compound

Product 1

HCID 9967171HCID 9967171, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-1-(S′-tert-butylcysteinyl)pyrrolidine-2-carbonitrile trifluoroacetate (1000 mg, 0.27 mmol; prepared according to Jenkins et al., WO95/15309), ethylchloroformate (35 mg, 0.32 mmol) and triethylamine (50 mg, 0.50 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.; 8:2) yielding a white solid identified as the title compound (30 mg, 0.092 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.; 8:2)
  6. customyielding a white solid

Sources & evidence

ORD record
ord-365ebabd455344ca98a76c761a4864c9
Source dataset
uspto-grants-2007_01
Patent number
US07169806B2

Reaction notes

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