Triethylamine → HCID 10642198, compound

HRID 1289253Notes

Reaction equation

HRID 1289253 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][OH:19])[C:13]([O-:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].[CH3:32]S(OCCCCC([O-])=O)(=O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][O:19][S:28]([CH3:27])(=[O:30])=[O:29])[C:13]([O:15][CH3:32])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131720634HCID 131720634, compoundHCID 131720635HCID 131720635, compound

Product 1

HCID 10642198HCID 10642198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl ((2S)-2-[N-(benzyloxycarbonyl)amino]-5-hydroxy-pentanoate (1.84 g, 6.98 mmol) in dichloromethane (27 ml) cooled to -10° C. under argon was added triethylamine (1.057 g, 10.47 mmol) and then methanesulphonyl chloride (0.99 g, 8.72 mmol) over a 2 minute period. Stirring was continued for 35 minutes while the temperature was maintained below 0° C. The reaction mixture was then diluted with dichloromethane (200 ml) and washed with water (100 ml), 10% aqueous citric acid (2×100 ml), saturated aqueous sodium bicarbonate (100 ml) and dilute brine (100 ml), dried (Na2SO4) and concentrated in vacuo to a yellow oil residue. Purification by column chromatography, on elution with 1:1 v/v ethyl acetate/hexanes, afforded methyl (2S)-2-{N-(benzyloxycarbonyl)amino!-5-(methylsulphonyloxy)-pentanoate as a colourless viscous oil (2.40 g, 96%);

Workup

  1. temperaturewas maintained below 0° C
  2. washwashed with water (100 ml), 10% aqueous citric acid (2×100 ml), saturated aqueous sodium bicarbonate (100 ml) and dilute brine (100 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo to a yellow oil residue
  5. customPurification by column chromatography
  6. washon elution with 1:1 v/v ethyl acetate/hexanes
  7. customafforded methyl (2S)-2-{N-(benzyloxycarbonyl)amino

Sources & evidence

ORD record
ord-fe2b015c7aed44e998bda8a1410aeac8
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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