L-Tyrosine → HCID 13146039, compound

HRID 851151Notes

Reaction equation

HRID 851151 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]([CH2:43][CH3:44])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH2:41][CH3:42])=[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.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]([CH2:43][CH3:44])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH2:41][CH3:42])=[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

6

Reactant 5

HCID 6057L-TyrosineHCID 6137L-Methionine2×HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13146037HCID 13146037, compound

Product 1

HCID 13146039HCID 13146039, compound

Procedure

To 0.50 g of BOC-Tyr-(D)-Met(O)-Gly-EtPhe-NHNHCOCH2CH3 were added 0.5 ml of anisole and 5 ml of TFA, and the mixture was shaken for 10 minutes. The solvent was distilled off, and ether was added to recover by filtration the product in the form of powder. The product was subjected to ion exchange on Amberlite IRA 410 (acetic acid type), and then poured on a column (2.2×120 cm) of Cephadex LH-20. The elution was conducted with 0.1 N acetic acid, and the fractions of 300 to 350 ml were collected and lyophilized. Yield: 0.35 g [α]D24 +18.5° (c=0.49, MeOH), Rf2, 0.24. Amino Acid analysis (4% thioglycolic acid/6 N hydrochloric acid hydrolysis): Gly 1.00(1), Met 1.05(1), Tyr 0.97(1).

Workup

  1. distillationThe solvent was distilled off
  2. additionether was added
  3. filtrationto recover by filtration the product in the form of powder
  4. additionpoured on a column (2.2×120 cm) of Cephadex LH-20
  5. washThe elution
  6. customthe fractions of 300 to 350 ml were collected
  7. customAmino Acid analysis (4% thioglycolic acid/6 N hydrochloric acid hydrolysis)

Sources & evidence

ORD record
ord-e45a59347e7241d1af90b2b2360b4420
Source dataset
uspto-grants-1983_05
Patent number
US04382923

Reaction notes

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