Triethylamine → HCID 178472497, compound

HRID 271346Notes

Reaction equation

HRID 271346 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178472486HCID 178472486, compound

Product 1

HCID 178472497HCID 178472497, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice cold solution of 1.8 g of cis-4-hydroxy-cyclohexanecarboxylic acid ethyl ester, and 2.8 mL of triethylamine, in 25 mL of dichloromethane was added 0.85 mL of methane-sulfonyl chloride drop-wise over 10 min. The mixture was allowed to stir for 30 min, then concentrated under reduced pressure and diluted with 50 mL of ether and washed with 25 mL of 10% HCl, 25 mL of water, 25 mL of saturated sodium carbonate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude mesylate, 2.5 g, was used without further purification: 1H NMR (400 MHz, CDCl3) 4.92 (m, 1H), 4.15 (q, 2H), 3.02 (s, 3H), 2.4 (m, 1H), 2.05 (m, 2H), 1.92 (m, 2H), 1.62-1.4 (complex m, 4H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with 50 mL of ether
  3. washwashed with 25 mL of 10% HCl, 25 mL of water, 25 mL of saturated sodium carbonate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mesylate, 2.5 g, was used without further purification

Sources & evidence

ORD record
ord-8d2d9d2afbd24808a28e9caefcbb4497
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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