Methanol → HCID 178476726, compound

HRID 1833326Notes

Reaction equation

HRID 1833326 reaction equation
C(O[C:9]([NH:11][C@H:12]([C:19]([N:21]1[CH2:33][CH2:32][CH2:31][C@H:22]1[C:23]([NH:25][CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:24])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10])C1C=CC=CC=1.[CH3:34][OH:35]>[Pd]>[C:28]([OH:29])(=[O:35])[CH3:27].[NH:11]1[C:34](=[O:35])[CH2:14][CH2:13][C@H:12]1[C:9]([NH:11][C@H:12]([C:19]([N:21]1[CH2:33][CH2:32][CH2:31][C@H:22]1[C:23]([NH:25][CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:24])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 178513928HCID 178513928, compound

Product 1

HCID 178476726HCID 178476726, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

1.0 g of benzyloxycarbonyl-L-histidyl-L-prolyl-β-alaninamide were dissolved in 50 ml of methanol and hydrogenated with the addition of palladium/carbon. The catalyst was filtered off and the filtrate concentrated in vacuo. The residue was dissolved in 10 ml of dimethylformamide and treated with 0.9 g of L-pyroglutamic acid pentachlorophenyl ester. The mixture was stored for 24 hours at room temperature and then concentrated in vacuo. The residue was dissolved in water and chromatographed on a Dowex 2 column (OH form). The fractions which were uniform in a thin-layer chromatogram were combined, acidified with acetic acid and lyophilised. Yield: 0.8 g. [α]D25 = -82.2° (c = 1 in 1 N acetic acid).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in 10 ml of dimethylformamide
  4. additiontreated with 0.9 g of L-pyroglutamic acid pentachlorophenyl ester
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in water
  7. customchromatographed on a Dowex 2 column (OH form)

Sources & evidence

ORD record
ord-2176d9fe7f0041c4b4bb0715e919ac72
Source dataset
uspto-grants-1978_01
Patent number
US04066635

Reaction notes

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