tert-Butoxycarbonyl-L-isoleucine → L-Isoleucine

HRID 1638575Notes

Reaction equation

HRID 1638575 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

3

Reactant 1

HCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 6306L-IsoleucineYield 88%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Boc-Ile-AMP (0.32 g, 1.0 mmole) is stirred in 10 ml of TFA-CH2Cl2 (1:1, v/v) for 30 minutes. TFA and CH2Cl2 are removed in vacuo and the residue is held under vacuum overnight. The residue is extracted with EtOAc and 5 ml of saturated aqueous NaHCO3. The organic layers are filtered through Na2SO4 and concentrated. The crude product is chromatographed on silica gel using 4% MeOH-CH2Cl2 (NH4OH sat'd) to give 0.194 g (88%) of Ile-AMP.

Workup

  1. customTFA and CH2Cl2 are removed in vacuo
  2. customis held under vacuum overnight
  3. extractionThe residue is extracted with EtOAc and 5 ml of saturated aqueous NaHCO3
  4. filtrationThe organic layers are filtered through Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is chromatographed on silica gel using 4% MeOH-CH2Cl2 (NH4OH sat'd)

Sources & evidence

ORD record
ord-92ac23d66b264b41983997a56d16d451
Source dataset
uspto-grants-1989_11
Patent number
US04880781

Reaction notes

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