Trityl chloride → HCID 21311272, compound

HRID 1584085Notes

Reaction equation

HRID 1584085 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:4]1=[O:5].C(N(CC)CC)C.Cl[C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[C:20]1([C:19]([NH:2][C@@H:3]2[CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:4]2=[O:5])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 51358597(3R)-3-Aminoazepan-2-one--hydrogen chloride (1/1)

Product 1

HCID 21311272HCID 21311272, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 173 g of (R)-α-amino-ε-caprolactam hydrochloride, 266 g of triethylamine and 1,700 ml of chloroform, 293 g of chlorotriphenylmethane was added portionwise under ice-cooling. The resulting mixture was stirred for an hour under the same conditions, and then for two hours at room temperature. The reaction mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and to the resultant oily residue 600 ml of n-hexane-ethyl acetate (2:1) mixture was added under heating and stirring. The crystalline precipitates obtained were collected by filtration, washed with 1,000 ml of n-hexane-ethyl acetate (10:1) mixture and dried to provide 290 g of (R)-α-triphenylmethylamino-ε-caprolactam, m.p. 189° C.

Workup

  1. additionwas added portionwise under ice-
  2. temperaturecooling
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionto the resultant oily residue 600 ml of n-hexane-ethyl acetate (2:1) mixture was added
  7. temperatureunder heating
  8. stirringstirring
  9. customThe crystalline precipitates
  10. customobtained
  11. filtrationwere collected by filtration
  12. washwashed with 1,000 ml of n-hexane-ethyl acetate (10:1) mixture
  13. customdried

Sources & evidence

ORD record
ord-50de8f9c372a4f72a0f6b12d08ff6675
Source dataset
uspto-grants-1999_08
Patent number
US05932568

Reaction notes

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