HCID 12888625, compound → HCID 12888627, compound

HRID 126786Notes

Reaction equation

HRID 126786 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[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.FC(F)(F)C(O)=O.O.CO.C(O)(=O)C.C(O)C.CCOCC>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([NH:29][C@H:30]([C:35]([NH2:37])=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=[O:28])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

7

Reactant 1

HCID 12888625HCID 12888625, compound

Product 1

HCID 12888627HCID 12888627, compoundYield 74%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 86607755Acetic acid methanol waterSolvent2×

Procedure

A solution of 2.2 g of Boc-Tyr-DAla-Phe-Met-NH2 in 20 ml of 10% anisole in trifluoroacetic acid (TFA) was stirred for 30 min. Evaporation of the solvent gave a residue which was dissolved in 20 ml of water:methanol:acetic acid (94:5:1) and applied to a column of Amberlite XAD-2 (44-74 μm, 2.7×60 cm). The sample was eluted at 6 ml/min with a convex gradient formed from 2 L of water:methanol:acetic acid (94:5:1) into which was fed methanol:water:acetic acid (50:49:1). Evaporation of the product peak gave a syrup which was dissolved in 100 ml of ethanol and diluted with 100 ml of ether to give 1.37 g (66%) of H-Tyr-DAla-Phe-Met-NH2.HOAc, m.p. 210°-211° C., [α]D25 =45.21° (c, 1.00 in 10% acetic acid).

Workup

  1. customEvaporation of the solvent
  2. customgave a residue which
  3. washThe sample was eluted at 6 ml/min with a convex gradient
  4. customformed from 2 L of water:methanol:acetic acid (94:5:1) into which
  5. customEvaporation of the product peak
  6. customgave a syrup which

Sources & evidence

ORD record
ord-7574e91421d14e569bd9561e967f130c
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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