Carbon Dioxide → H-His-Lys(Boc)-OMe

HRID 1982307Notes

Reaction equation

HRID 1982307 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:9]([NH:11][C@H:12]([C:25]([O:27][CH3:28])=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.Cl.C(=O)=O>CO>[NH2:1][C@H:2]([C:9]([NH:11][C@H:12]([C:25]([O:27][CH3:28])=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 178501447Z-His-Lys(Boc)-OMe

Product 1

HCID 178501448H-His-Lys(Boc)-OMe

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.6 g of Z-His-Lys(Boc)-OMe [S. Guttman et al., Helv. Chim. Acta 52, 1789 (1969)] are dissolved in 33 ml of MeOH, 3 ml of 1N HCl and 160 mg of Pd-on-carbon (10% pd) are added thereto, and hydrogenation is carried out with CO2 -absorption until saturation. After filtering off the catalyst, the whole is concentrated, the oily residue is dissolved in 20 ml of DMF and again concentrated to approximately 10 ml, yielding H-His-Lys(Boc)-OMe in the form of a solution which is immediately further processed in stage 2.2.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe whole is concentrated
  3. dissolutionthe oily residue is dissolved in 20 ml of DMF
  4. concentrationagain concentrated to approximately 10 ml

Sources & evidence

ORD record
ord-041d176aa1c94211a19bf4f19e787129
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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