Sodium Bicarbonate → HCID 15159823, compound

HRID 358915Notes

Reaction equation

HRID 358915 reaction equation
[C:1]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:28]([NH:30][CH2:31][CH2:32][C:33]([CH:35]=[N+]=[N-])=[O:34])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCOCC.[ClH:43].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:4]([O:3][C:1]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:28]([NH:30][CH2:31][CH2:32][C:33]([CH2:35][Cl:43])=[O:34])=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:2])([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10953452Ether hydrochlorideHCID 54177731HCID 54177731, compound

Product 1

HCID 15159823HCID 15159823, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boc-tryptophyl-leucyl-β-alanyl-diazomethane (Section 5.7.1) (0.24 g, 0.47 mmol) was dissolved in ethyl acetate (50 ml). Ether/HCl (40 ml) was added followed by 5% NaHCO3 (60 ml) 1 minute later. The mixture was agitated to neutralise the acid and the aqueous layer was removed. The organic phase was dried over magnesium sulphate and reduced to dryness. The peptide was recrystallised from ethyl acetate/petrol ether (40°/60° C.) and then diethyl ether/petrol ether (40°/60° C.). Yield 0.2 g (82%), m.p. 79°-81° C. The product was homogeneous as judged by tlc in chloroform/methanol (4:1) (Rf 0.770) or chloroform/methanol (1:1) (Rf 0.777). (Found: C, 59.83; H, 7.35; N, 10.81. C26H37O5N4Cl1 requires C, 60.00; H, 7.11; N, 10.77%).

Workup

  1. customthe aqueous layer was removed
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customThe peptide was recrystallised from ethyl acetate/petrol ether (40°/60° C.)
  4. customdiethyl ether/petrol ether (40°/60° C.)

Sources & evidence

ORD record
ord-f071fb5195ad4826a586ff68b06e8bd0
Source dataset
uspto-grants-1991_03
Patent number
US04997950

Reaction notes

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