Trityl chloride → HCID 11360286, compound

HRID 2088858Notes

Reaction equation

HRID 2088858 reaction equation
C(N(CC)CC)C.Cl.[NH:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([NH2:13])=[O:12].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl.ClCCl>[C:17]([N:9]1[CH2:16][CH2:15][CH2:14][C@@H:10]1[C:11]([NH2:13])=[O:12])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochloride

Product 1

HCID 11360286HCID 11360286, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Under cold conditions (ice bath) and under an inert atmosphere, 10 ml of triethylamine (69.7 mmol) are added to 5 g (33.2 mmol) of prolinamide hydrochloride suspended in chloroform (50 ml), and 9.7 g (34.9 mmol) of trityl chloride are then added portionwise. The reaction mixture is stirred at room temperature for 2 days. The reaction mixture is dissolved in dichloromethane (200 ml) and washed successively twice with HCl solution (1N) (150 ml), with water (150 ml), with saturated NaHCO3 solution (150 ml) and with saturated NaCl solution (150 ml). The organic phase is dried (Na2SO4), filtered and evaporated under reduced pressure. The residue is recrystallized from 20 ml of hot ethanol, to give 11 g of compound in the form of white crystals. Yield=93%. Melting point: 162° C.

Workup

  1. washwashed successively twice with HCl solution (1N) (150 ml), with water (150 ml), with saturated NaHCO3 solution (150 ml) and with saturated NaCl solution (150 ml)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue is recrystallized from 20 ml of hot ethanol

Sources & evidence

ORD record
ord-6f04ae3f1e4a4411b652f57381602724
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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