HCID 131719355, compound → HCID 131719354, compound

HRID 1441186Notes

Reaction equation

HRID 1441186 reaction equation
[NH:1]([CH3:52])[C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:26]([NH:28][C@H:29]([C:41]([NH:43][C@H:44]([C:49]([OH:51])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:30][C:31](=[O:40])[O:32]CC1C=CC=CC=1)=[O:27])[CH2:18][C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1>[Pd].CN(C=O)C.CCO>[NH:1]([CH3:52])[C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:26]([NH:28][C@H:29]([C:41]([NH:43][C@H:44]([C:49]([OH:51])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:30][C:31](=[O:32])[OH:40])=[O:27])[CH2:18][C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 131719355HCID 131719355, compoundHCID 131719356HCID 131719356, compound

Product 1

HCID 131719354HCID 131719354, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

More specifically exemplified, the protected peptide, DAT-N-Me-Val-Ile-Asp(NEt2)-Asp(OBzl)-Leu-OH was assembled by the preceding procedure on a BHA photoresin using BOP/HOBt as the coupling agent, followed by cleavage of the resulting protected peptide resin by photolysis under argon at -5° for 6 h. DMF:EtOH (4:1) was used as the photolysis medium. Deprotection of the cleavage product was effected by hydrogenolysis using 5% Pd/C as catalyst. Purification of the product was done by HPLC, the product being dissolved in 0.1N aqueous NH4OH solution and the solution adjusted to pH6 with 0.1N aqueous AcOH. Whatman Partisil® 100DS-3 C-18 column (2.2×50 cm2), 10 micron particle size, was used. Elution was done with a gradient of acetonitrile and 0.06% aqueous TFA. Pure fractions (determined by analytical HPLC) were pooled and lyophilized to give DAT-N-Me-Val-Ile-Asp(NEt2)-Asp-Leu-OH. MS: 791 (M+H)+.

Workup

  1. customat -5°
  2. customfor 6 h
  3. customPurification of the product
  4. dissolutionthe product being dissolved in 0.1N aqueous NH4OH solution
  5. washElution

Sources & evidence

ORD record
ord-23d4967d04354312b7972a4b4f963f14
Source dataset
uspto-grants-1996_03
Patent number
US05502036

Reaction notes

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