Ammonia → Boc-Leu-Leu-NH2

HRID 276712Notes

Reaction equation

HRID 276712 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:7]([NH:9][C@H:10]([C:15](O)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C[N:26]1CCOCC1.ClC(OCC(C)C)=O.N>C1COCC1>[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH2:26])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 7019882(S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid

Product 1

HCID 7329741Boc-Leu-Leu-NH2Yield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Boc-Leu-Leu-OH (Bachem, 43.6 mmol) is dissolved in THF (250 ml) and N-methylmorpholine (43.6 mmol) is added. The mixture is cooled to −20° C. and isobutyl chloroformate (43.6 mmol) is added dropwise. The mixture is stirred for 10 min. and then a 25% aqueous solution of ammonia (52.3 mmol) is added at −20° C. The mixture is stirred for 3 hours at −20° C. to −10° C. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate and evaporated. The crude product is suspended in diethylether and the solid filtered of and dried (vacuum). 14.2 g of a white powder with mp. 155-156° C., Rf=0.5 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. stirringThe mixture is stirred for 3 hours at −20° C. to −10° C
  2. customAfter evaporation of the solvent
  3. extractionthe residue is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)

Sources & evidence

ORD record
ord-1d37bc99e4fd4aef8ed55fd754dae84b
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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