HCID 131710008, compound → Glycine, N-(N-L-methionyl-L-leucyl)-

HRID 1580907Notes

Reaction equation

HRID 1580907 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]>FC(F)(F)C(O)=O>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

3

Reactant 1

HCID 131710008HCID 131710008, compound

Product 1

HCID 7020116Glycine, N-(N-L-methionyl-L-leucyl)-

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6.9 g of BOC-Met-Leu-Gly-OH are dissolved in 70 ml of 90 % strength trifluoracetic acid and left to stand for one hour at 20°C. Thereafter the solution is concentrated, mixed with 150 ml of ether whilst stirring and left to stand overnight at -10°C. The resulting precipitate is filtered off and again stirred with 100 ml of ether, filtered off, twice washed with ether and dried in vacuo over sodium hydroxide. Melting point 134°-135°C; Rf7 = 0.52 (on silica gel).

Workup

  1. waitleft
  2. concentrationThereafter the solution is concentrated
  3. additionmixed with 150 ml of ether
  4. waitleft
  5. waitto stand overnight at -10°C
  6. filtrationThe resulting precipitate is filtered off
  7. stirringagain stirred with 100 ml of ether
  8. filtrationfiltered off
  9. washtwice washed with ether
  10. dry with materialdried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-4926b56863cc4d26a6a8cde8139d8e32
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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