Methyl chloroformate → HCID 69517019, compound

HRID 1375739Notes

Reaction equation

HRID 1375739 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].Cl[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>ClCCl>[CH3:21][O:20][C:18]([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:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69520335HCID 69520335, compound

Product 1

HCID 69517019HCID 69517019, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-1-(isoleucyl)pyrrolidine-2-carbonitrile hydrochloride (300 mg, 1.22 mmol; prepared according to Jenkins et al., WO95/15309), methyl chloroformate (125 mg, 1.3 mmol) and triethylamine (150 mg, 1.50 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 (EtOAc:Pet. Ether 60–80° C.; 4:6) yielding a colourless oil identified as the title compound (310 mg, 1.16 mmol, 95%).

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 (EtOAc:Pet. Ether 60–80° C.; 4:6)
  6. customyielding a colourless oil

Sources & evidence

ORD record
ord-93eb7de385724347b96e63aba4b1fbb1
Source dataset
uspto-grants-2007_01
Patent number
US07169806B2

Reaction notes

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