Boron Trichloride → 60067-16-5

HRID 1388967Notes

Reaction equation

HRID 1388967 reaction equation
C(OC([NH:11][C@H:12]([C:28]([NH:30][CH2:31][C:32]([N:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=1[C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:35])=[O:33])=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.B(Cl)(Cl)[Cl:52]>ClCCl>[ClH:42].[ClH:52].[NH2:11][C@H:12]([C:28]([NH:30][CH2:31][C:32]([N:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=1[C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH3:35])=[O:33])=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86734480HCID 86734480, compound

Product 1

HCID 7056036560067-16-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

1.4 g of (Nα, Nε -bisbenzyloxycarbonyl-L-lysyl)-N-(2-benzoyl-4-chlorophenyl)-N-methylglycinamide were dissolved in 30 ml of dry dichloromethane, cooled to approximately -70° C. and treated, while stirring, with 2 ml of pre-cooled boron trichloride. The mixture was stirred under anhydrous conditions at approximately -70° C. for 30 minutes and then allowed to warm slowly to room temperature over a period of 2 hours. The mixture was evaporated to dryness in vacuo, the residue re-dissolved in 30 ml of fresh dry dichloromethane and the solution again evaporated to dryness in vacuo. This operation was repeated twice using dichloromethane and then four times using methanol in order to remove the residual boron compounds as volatile trimethyl borate. A concentrated methanolic solution of the residue was added slowly to 750 ml of anhydrous diethyl ether with vigorous stirring, the solid hygroscopic product collected by filtration and dried in vacuo. This product was dissolved in 30 ml of water, shaken with three 20 ml portions of ethyl acetate to remove traces of 5-chloro-2-methylaminobenzophenone and the aqueous solution lyophilised to give 0.7 g of L-lysyl-N-(2-benzoyl-4-chlorophenyl)-N-methylglycinamide dihydrochloride which was identical to that described in part (i) of this Example.

Workup

  1. additiontreated
  2. temperatureto warm slowly to room temperature over a period of 2 hours
  3. customThe mixture was evaporated to dryness in vacuo
  4. dissolutionthe residue re-dissolved in 30 ml of fresh dry dichloromethane
  5. customthe solution again evaporated to dryness in vacuo
  6. customto remove the residual boron compounds as volatile trimethyl borate
  7. additionA concentrated methanolic solution of the residue was added slowly to 750 ml of anhydrous diethyl ether with vigorous stirring
  8. filtrationthe solid hygroscopic product collected by filtration
  9. customdried in vacuo
  10. dissolutionThis product was dissolved in 30 ml of water
  11. stirringshaken with three 20 ml portions of ethyl acetate
  12. customto remove traces of 5-chloro-2-methylaminobenzophenone

Sources & evidence

ORD record
ord-67cc0b7da92b49f499dc7f8d81e789f9
Source dataset
uspto-grants-1981_01
Patent number
USRE030473

Reaction notes

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