Hydrochloric Acid → HCID 178512901, compound

HRID 1414682Notes

Reaction equation

HRID 1414682 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([N:15]1[CH2:56][CH2:55][CH2:54][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:39]([NH:41][C@H:42]([C:51]([NH2:53])=[O:52])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=1)=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+]([O-])=O.Cl.N[C@H](C(O)=O)CCCNC(=N)N.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.N[C@H](C(O)=O)CC1C=CC=CC=1>[Pd].O.C(O)(=O)C>[NH2:1][C@H:2]([C:13]([N:15]1[CH2:56][CH2:55][CH2:54][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:39]([NH:41][C@H:42]([C:51]([NH2:53])=[O:52])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=1)=[O:40])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:12]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6057L-TyrosineHCID 6140L-PhenylalanineHCID 178418600HCID 178418600, compoundHCID 178512178HCID 178512178, compound

Product 1

HCID 178512901HCID 178512901, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 30 ml. of acetic acid was dissolved 500 mg. of Z-Arg(NO2)-Pro-Phe-Phe-Tyr-NH2, and catalytic reduction was carried out with Pd-black as a catalyst for 20 hours. The catalyst was filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 50 ml. of water and, after the small amounts of insolubles were filtered off, the filtrate was lyophilized. The product was dissolved in 5 ml. of water and the solution was applied on a column (1.8 × 9 cm) of carboxymethyl-sephadex. Gradient elution was carried out with 0.1M aqueous ammonium acetate (400 ml.) and 1M aqueous ammonium acetate (400 ml.). The fractions from 250 ml. to 370 ml. were pooled and lyophilized to yield 250 mg. (52.3 %) of a white fluffy product. [α]D24 -41.9° (c=0.47 %, water). Amino acid analysis (hydrolysis with HCl): Arg, 1.00;Pro, 1.05; Tyr, 0.91; Phe, 1.96;(peptide content 86.5 %).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml
  4. filtrationof water and, after the small amounts of insolubles were filtered off
  5. dissolutionThe product was dissolved in 5 ml
  6. washGradient elution
  7. customto yield 250 mg

Sources & evidence

ORD record
ord-68c06e1ab20c47c3aea036b125c822ac
Source dataset
uspto-grants-1977_01
Patent number
US04001199

Reaction notes

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