Carbon Dioxide → Boc-Leu-DTrp-NHNH2

HRID 129986Notes

Reaction equation

HRID 129986 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([O:23]C)=O)[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O.[NH2:33][NH2:34].C(=O)=O>CN(C=O)C>[NH:1]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:33][NH2:34])=[O:23])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 24654Hydrazine hydrate (1:1)HCID 14504288Boc-Leu-DTrp-OMe

Product 1

HCID 11070055Boc-Leu-DTrp-NHNH2

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in (1) (430 mg) in DMF (10 ml) was added hydrazine monohydrate (1.0 ml) at room temperature and the solution was stirred overnight. To the reaction mixture was added dry-ice and the resulting solution was concentrated to give a residue, which was triturated with water to afford the product (406 mg). FAB-MS(m/e,(C22H33N5O4 +H)+):432

Workup

  1. concentrationthe resulting solution was concentrated
  2. customto give a residue, which
  3. customwas triturated with water

Sources & evidence

ORD record
ord-d0d018fd4cca4b5cad0d39bdf3f2cb0c
Source dataset
uspto-grants-1995_11
Patent number
US05470833

Reaction notes

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