Triethylamine → N-tosylsarcosyl-L-prolinol

HRID 467157

Reaction equation

HRID 467157 reaction equation
[S:1]([N:11]([CH2:13][C:14]([OH:16])=O)[CH3:12])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH:17]1[CH2:23][CH2:22][CH2:21][C@H:18]1[CH2:19][OH:20].C(N(CC)CC)C.[Cl-].ClC1N(C)C=C[N+]=1C>C(Cl)Cl>[S:1]([N:11]([CH2:13][C:14]([N:17]1[CH2:23][CH2:22][CH2:21][C@H:18]1[CH2:19][OH:20])=[O:16])[CH3:12])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 802555[Methyl-(toluene-4-sulfonyl)-amino]-acetic acidHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chloride

Product 1

HCID 15132632N-tosylsarcosyl-L-prolinolYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-tosylsarcosine (60 g, 247 mmol) and L-prolinol (24.9 g, 247 mmol) are dissolved in methylene chloride (800 ml), and triethylamine (102.5 ml, 741 mmol) is added thereto. To this mixture is added dropwise, over a period of one hour under water-cooling, a solution of 2-chloro-1,3-dimethylimidazolium chloride (DMC) (62.6 g, 371 mmol) in methylene chloride. The mixture is further stirred for 2 hours at room temperature and then the reaction liquid is washed successively with water (1 l, a saturated aqueous solution of sodium hydrogen carbonate (1 l, 1N hydrochloric acid (1 l) and water (1 l). The organic layer is dried over anhydrous magnesium sulfate and filtered, and the filtrate is concentrated to dryness under reduced pressure to give N-tosylsarcosyl-L-prolinol (82.1 g, 102%).

Workup

  1. additionTo this mixture is added dropwise, over a period of one hour under water-
  2. temperaturecooling
  3. customthe reaction liquid
  4. washis washed successively with water (1 l
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8d7b8743ed1f42128e00648d37aca7f0
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Linked notes

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