HCID 131715392, compound → HCID 131715391, compound

HRID 247509Notes

Reaction equation

HRID 247509 reaction equation
[NH:1]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:2]([C:7]([NH:9][C@H:10]([C:16]([NH:18][C@H:19]([C:31]([NH:33][C@H:34]([C:39]([NH:41][C@H:42]([C:47]([NH:49][NH:50]C(OCC(Cl)(Cl)Cl)=O)=[O:48])[CH2:43][CH2:44][S:45][CH3:46])=[O:40])[C@H:35]([CH2:37][CH3:38])[CH3:36])=[O:32])[CH2:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:17])[CH2:11][CH2:12][C:13](=[O:15])[NH2:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]>CN(C=O)C.C(O)(=O)C.[Zn]>[NH:1]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:2]([C:7]([NH:9][C@H:10]([C:16]([NH:18][C@H:19]([C:31]([NH:33][C@H:34]([C:39]([NH:41][C@H:42]([C:47]([NH:49][NH2:50])=[O:48])[CH2:43][CH2:44][S:45][CH3:46])=[O:40])[C@H:35]([CH2:37][CH3:38])[CH3:36])=[O:32])[CH2:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:17])[CH2:11][CH2:12][C:13](=[O:15])[NH2:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 1

HCID 131715392HCID 131715392, compound

Product 1

HCID 131715391HCID 131715391, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

17.9 g (17.5 mM) of Boc-Leu-Gln-Asp(OBzl)-Ile-Met-NH-NH-Troc are dissolved in a mixture of 200 ml of DMF and 50 ml of acetic acid and strongly stirred with mechanical stirring means. 11.5 g of powdered zinc (300 mesh=47 μm) are added in one operation and stirring is continued for 1 hour and 40 mins. at ambient temperature. The solid is drained, washed in DMF and the filtrate is introduced in 740 g of ice. The mixture is left to stand for one night, and then drained. The precipitate is washed with large quantities of water and dried in the open, then in a desiccator +P205.

Workup

  1. stirringwith mechanical stirring means
  2. stirringstirring
  3. customat ambient temperature
  4. washwashed in DMF
  5. additionthe filtrate is introduced in 740 g of ice
  6. waitThe mixture is left
  7. waitto stand for one night
  8. washThe precipitate is washed with large quantities of water
  9. customdried in the open, then in a desiccator +P205

Sources & evidence

ORD record
ord-d78c70dd179a44b6bb6d36b58f46b56f
Source dataset
uspto-grants-1987_11
Patent number
US04707541

Reaction notes

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