HCID 131714156, compound → HCID 131714155, compound

HRID 2164482Notes

Reaction equation

HRID 2164482 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([NH:46][C@H:47]([C:54]([NH:56][C@H:57]([C:67]([O:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:68])[CH2:58][CH2:59][C:60](=[O:66])[O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:55])[CH2:48][O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:45])[CH2:38][O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:35])[C@@H:27]([CH3:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:24])[CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3]>CN(C=O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([NH:46][C@H:47]([C:54]([NH:56][C@H:57]([C:67]([O:69][C:70]1[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=1)=[O:68])[CH2:58][CH2:59][C:60](=[O:66])[O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:55])[CH2:48][O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:45])[CH2:38][O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:35])[C@@H:27]([CH3:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:24])[CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:12])[CH:8]([CH3:9])[CH3:10])=[O:5])[CH3:3]

Participants

4

Reactant 1

HCID 131714156HCID 131714156, compound

Product 1

HCID 131714155HCID 131714155, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Z-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (20.16 g; 16.8 mmol) in DMF (400 mL) was hydrogenated with 5% Pd-BaSO4 (10 g) for 2 h in a Vibromixer apparatus. The reaction mixture was filtered through celite which was washed with additional DMF (228 mL). The combined filtrate was used directly in the next stage of synthesis. A portion of the material was precipitated by addition of H2O, filtered and dried in vacuo; mp >275°; [α]D25 -9.28° (c 1, TFE); Rf 0.77 (n-BuOH:AcOH:Pyr:H2O; 4-7-1-1); Rf 0.65 (n-BuOH:H2O:AcOH:EtOAc; 1-1-1-1). Anal. calc. for C53H89N7O15.H2O (1082.36): C, 58.82; H, 8.48; N, 9.06. Found: C, 59.11; H, 8.56; N, 9.23.

Workup

  1. filtrationThe reaction mixture was filtered through celite which
  2. washwas washed with additional DMF (228 mL)
  3. customThe combined filtrate was used directly in the next stage of synthesis
  4. customA portion of the material was precipitated by addition of H2O
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c1c469f9c3274a1c87b03e1e8633078d
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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