تفاعل #1447112

ord-5ed23c939c864e90ad752df79c214073

معادلة التفاعل

CCN(CC)CC
Et3N
O=P(Cl)(Cl)Oc1cccc2ccccc12
1-naphthyl dichlorophosphate
CCCCOC(=O)[C@H](C)[NH3+].[Cl-]
(25)-1-butoxy-1-oxopropan-2-aminium chloride
CCCCOC(=O)[C@H](C)NP(=O)(Cl)Oc1cccc2ccccc12
n-Butyl N-[chloro(1-naphthyloxy)phosphoryl]-L-alaninate

المذيبات

ظروف التفاعل

درجة الحرارة
-78°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITthe reaction was left
  2. 2
    درجة الحرارةto warm to RT overnight
  3. 3
    أخرىAll volatiles were removed
  4. 4
    غسيلthe resulting white solid was washed with Et2O
  5. 5
    ترشيحfiltered
  6. 6
    أخرىevaporated in vacuo
  7. 7
    أخرىto obtain a colorless oil
  8. 8
    workup.ADDITIONas a 1:1 mixture of diastereoisomers

الإجراء التجريبي

To 1-naphthyl dichlorophosphate in DCM (0.086 M) was added (25)-1-butoxy-1-oxopropan-2-aminium chloride (1.0 eq.). After cooling to −78° C., neat Et3N (2.0 eq.) was added and the reaction was left to warm to RT overnight. All volatiles were removed and the resulting white solid was washed with Et2O, filtered and evaporated in vacuo to obtain a colorless oil as a 1:1 mixture of diastereoisomers. 31P NMR (400 MHz, CDCl3): δ 8.39 and 8.11 ppm.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07879815B2uspto-grants-2011_02