Carbon Dioxide → HCID 178455961, compound

HRID 1982309Notes

Reaction equation

HRID 1982309 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:17]([NH:19][C@H:20]([C:33]([O:35][CH3:36])=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:18])[CH2:11][C:12]1[N:16]=[CH:15][NH:14][CH:13]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].O.C(O)C(F)(F)F.C(=O)=O>CO>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:17]([NH:19][C@H:20]([C:33]([O:35][CH3:36])=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[O:18])[CH2:11][C:12]1[N:16]=[CH:15][NH:14][CH:13]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 178455965HCID 178455965, compound

Product 1

HCID 178455961HCID 178455961, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8 g of Z-Ile-His-Lys(Boc)-OMe are suspended in a mixture of 80 ml of MeOH, 8 ml of H2O and 80 ml of trifluoroethanol, and hydrogenated with 800 mg of Pd-on-carbon (10% Pd) with CO2 -absorption until saturation, the initially undissolved material being dissolved. The catalyst is filtered off, the filtrate is concentrated to dryness and the resinous residue is crystallised from acetonitrile, yielding H-Ile-His-Lys(Boc)-OMe in the form of needles having a melting point of 129°-130°; Rf (I)=0.12; Rf (B)=0.14.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. customthe resinous residue is crystallised from acetonitrile

Sources & evidence

ORD record
ord-95a49b717979440aadbf0bcee3f18bd7
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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