Glycine → HCID 127165, compound

HRID 851150Notes

Reaction equation

HRID 851150 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH2:42][CH3:43])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH3:41])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O.NCC(O)=O.N[C@H](C(O)=O)CCSC.N[C@H](C(O)=O)CC1C=CC(O)=CC=1>>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH2:42][CH3:43])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH3:41])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

7

Reactant 6

HCID 750GlycineHCID 6057L-TyrosineHCID 6137L-MethionineHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13146034HCID 13146034, compound

Product 1

HCID 127165HCID 127165, compound

Procedure

To 0.20 g of BOC-Tyr-(D)-Met(O)-Gly-EtPhe-NHNHCOCH3 were added 0.2 ml of anisole and 4 ml of TFA, and the mixture was shaken for 10 minutes. Then, the solvent was distilled off and ether was added to the residue of thereby recover by filtration the product in the form of powder. The product was subjected to ion exchange with Amberlite IRA 410 (acetic acid type) and then poured on a column (2.2×120 cm) of Sephadex LH-20. The elution was conducted with 0.1 N acetic acid, and the fractions of 285 to 340 ml were collected and lyophilized. Yield: 0.14 g, [α]D24 +20.4° (c=0.50, MeOH), Rf2 0.22. Amino acid analysis (4% thioglycolic acid/6 N hydrochloric acid hydrolysis): Gly 0.99(1), Met 1.00(1), Tyr 1.04(1).

Workup

  1. distillationThen, the solvent was distilled off
  2. additionether was added to the residue
  3. filtrationof thereby recover by filtration the product in the form of powder
  4. additionpoured on a column (2.2×120 cm) of Sephadex LH-20
  5. washThe elution
  6. customthe fractions of 285 to 340 ml were collected
  7. customAmino acid analysis (4% thioglycolic acid/6 N hydrochloric acid hydrolysis)

Sources & evidence

ORD record
ord-6835792461ae4a16a9a01d40de7e496f
Source dataset
uspto-grants-1983_05
Patent number
US04382923

Reaction notes

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