Triethylamine → HCID 86595160, compound

HRID 1829812Notes

Reaction equation

HRID 1829812 reaction equation
[Si:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:17]=[CH:16]1)[CH2:12][CH2:13][OH:14])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(N(CC)CC)C>ClCCl>[Si:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:17]=[CH:16]1)[CH2:12][CH2:13][O:14][S:26]([CH3:25])(=[O:28])=[O:27])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69527792HCID 69527792, compound

Product 1

HCID 86595160HCID 86595160, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-3-pentyl]imidazole-4-carboxylate (500 mg, 1.4 mmol) and methanesulfonyl chloride (321 mg, 2.8 mmol) in dichloromethane (15 ml) was added dropwise triethylamine (284 mg, 2.8 mmol) at ice-bath temperature. After 1 h, the reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo to give ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxylate (642 mg, 105%) as a syrup. This material was used for the next reaction without further purification.

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69ffe4c14e2f4961a9d7f23bda8ff482
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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