Triethylamine → HCID 131725021, compound

HRID 1072650Notes

Reaction equation

HRID 1072650 reaction equation
Cl.[C:2]([O:6][C@H:7]([CH3:19])[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].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C(N(CC)CC)C>ClCCl>[CH2:24]([O:23][C:21]([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])[C@@H:7]([CH3:19])[O:6][C:2]([CH3:5])([CH3:3])[CH3:4])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 131725022HCID 131725022, compound

Product 1

HCID 131725021HCID 131725021, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-1-(O′-tert-butylthreoninyl)pyrrolidine-2-carbonitrile hydrochloride (35 mg, 0.12 mmol; prepared according to Jenkins et al., WO95/15309), benzyl chloroformate (32 mg, 0.13 mmol) and triethylamine (24 mg, 0.24 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: chloroform: methanol; 98:2) yielding a white solid identified as the title compound (47 mg, 0.12 mmol, 100%).

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: chloroform: methanol; 98:2)
  6. customyielding a white solid

Sources & evidence

ORD record
ord-0ad23be58000465fa1b69e3724f488ac
Source dataset
uspto-grants-2005_06
Patent number
US06911467B2

Reaction notes

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