L-Phenylalanine → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-

HRID 2419489Notes

Reaction equation

HRID 2419489 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCN(CC)CC.[NH:20]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:21]([C:26](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]>CN(C=O)C>[NH:20]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[C@H:21]([C:26]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 11047584HCID 11047584, compound

Product 1

HCID 10981745L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

H-Phe-OH (1.49 g, 9 mmol) fine powder was suspended in DMF (20 ml). After cooling at 0°, Et3N (1.26 ml, 9 mmol) was added, followed by Boc-Leu-pentafluorophenylester, i.e., Boc-Leu-OPfp (3.93 g, 9.9 mmol). It was stirred for 1 hr at 0° C and for 2.5 hr at room temperature. After filtration the solvent was evaporated and the residue was treated with H2O. The separated oil was extracted with EtOAc. The organic phase was washed with 10% citric acid, H2O, dried (Na2SO4) and evaporated to a smaller volume. Addition of petroleum ether and standing overnight in the refrigerator provided the product (XVI) which was recrystallized from EtOAc-petroleum ether to fine crystals, yield 2.3 g (67.6%); mp 104°-106° C; [α]D25 -3.40° (c 1, EtOH). Anal. Calcd for C20H30N2O5 (378.476): C, 63.47; H, 7.99; N, 7.40. Found: C, 63.46; H, 8.18; N, 7.49.

Workup

  1. temperatureAfter cooling at 0°
  2. filtrationAfter filtration the solvent
  3. customwas evaporated
  4. additionthe residue was treated with H2O
  5. extractionThe separated oil was extracted with EtOAc
  6. washThe organic phase was washed with 10% citric acid, H2O
  7. dry with materialdried (Na2SO4)
  8. customevaporated to a smaller volume
  9. additionAddition of petroleum ether
  10. waitstanding overnight in the refrigerator

Sources & evidence

ORD record
ord-c9bc524b711c461ea6537a05c40a94cb
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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