Bis(2-chloroethyl)amine → N-[N-(cholest-5-en-3beta-oxycarbonyl)glycyl]bis(2-chloroethyl)amine

HRID 622727Notes

Reaction equation

HRID 622727 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33](O)=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[Cl:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][Cl:42].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33]([N:39]([CH2:40][CH2:41][Cl:42])[CH2:38][CH2:37][Cl:36])=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 9533Bis(2-chloroethyl)amineHCID 10868DicyclohexylcarbodiimideHCID 14168269N-(cholest-5-en-3beta-oxycarbonyl)glycine

Product 1

HCID 86742447N-[N-(cholest-5-en-3beta-oxycarbonyl)glycyl]bis(2-chloroethyl)amineYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(cholest-5-en-3β-oxycarbonyl)glycine (160.8 mg) in dry tetrahydrofuran (50 ml) was added said bis(2-chloroethyl)amine (85.2 mg) and dicyclohexylcarbodiimide (61.9 mg) at 0° C. under blowing nitrogen gas and the mixture was stirred for 6 hours. After standing overnight (17 hours) at refrigerator, the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was solved in a mixture of chloroform and methanol (50:1) and was subjected to preparation column chromatography (PLC) eluting with a mixture of chloroform and methanol (50:1). The desired parts were gathered, extracted with a mixture of chloroform and methanol (4:1), filtered and concentrated under reduced pressure to give N-[N-(cholest-5-en-3β-oxycarbonyl)glycyl]bis(2-chloroethyl)amine (110 mg).

Workup

  1. customat 0° C.
  2. waitAfter standing overnight
  3. filtration(17 hours) at refrigerator, the reaction mixture was filtered
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was solved in a mixture of chloroform and methanol (50:1)
  6. customwas subjected to preparation column chromatography (PLC)
  7. washeluting with a mixture of chloroform and methanol (50:1)
  8. extractionextracted with a mixture of chloroform and methanol (4:1)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd559e4e847a4eec90e32acf59b57e58
Source dataset
uspto-grants-1988_09
Patent number
US04772594

Reaction notes

Loading…