Ammonium Hydroxide → N6-Trityl-Lysinamide

HRID 1836948

Reaction equation

HRID 1836948 reaction equation
[C:1]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]([C:27]([OH:29])=O)[NH2:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:31]>CN(C=O)C>[C:1]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]([C:27]([NH2:31])=[O:29])[NH2:26])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 13943552N6-Trityl-Lysine

Product 1

HCID 86584276N6-Trityl-LysinamideYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 2 (1.49 g, 3.71 mmol) in 10 ml DMF was cooled to −78° C. in a pressure tube. Ammonia gas was bubbled though the solution until approximately 1 ml has added. Ammonium hydroxide solution (12 ml, 185.6 mmol, 50+ equivalents) was then added, and the tube allowed to warm to room temperature. The mixture was then sonicated for 20 minutes and heated to 55° C. while stirring. After 24 hours, the solution was golden in color, after which it was removed from the oil bath and cooled to −78° C. for 5 minutes before removing pressure cap. The solution was then allowed to warm to room temperature, and the solvent removed by reduced pressure distillation. The product was purified by flash column chromatography (Silica Gel, 8% methanol/92% CH2Cl2). and isolated as a clear golden oil (0.987 g. Yield: 68%). 1H NMR (CDCl3, 300 MHz) δ1.3-1.6 (m, 4H), 1.76 (m, 2H), 2.13 (t,2H), 3.33 (t, 1H) 7.14-7.52 (m, 15H) 13C NMR (CDCl3) 75 MHz) δ23.8, 30.9, 35.2, 43.6, 55.3, 71.0, 126.3, 127.9, 128.8, 146.4, 178.3; ESI-MS calculated for C25H29N3O 387.52; found 388.4 [M++1].

Workup

  1. customAmmonia gas was bubbled though the solution until approximately 1 ml
  2. additionhas added
  3. customThe mixture was then sonicated for 20 minutes
  4. temperatureheated to 55° C.
  5. customafter which it was removed from the oil bath
  6. temperaturecooled to −78° C. for 5 minutes
  7. custombefore removing pressure
  8. customcap
  9. temperatureto warm to room temperature
  10. customthe solvent removed by reduced pressure distillation
  11. customThe product was purified by flash column chromatography (Silica Gel, 8% methanol/92% CH2Cl2)
  12. customand isolated as a clear golden oil (0.987 g. Yield: 68%)

Sources & evidence

ORD record
ord-bb7989a18dba48e0ad0c311cbdb2012d
Source dataset
uspto-grants-2004_08
Patent number
US06780856B2

Linked notes

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