Sulfuric Acid → HCID 86746043, compound

HRID 846312Notes

Reaction equation

S(=O)(=O)(O)O.[N:6]#[N:7].[C:8]([C@@H:11]([NH:20][C@H:21]([C:33]([OH:35])=O)[CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(=O)C(F)(F)F)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:10])N.[OH-:36].[Na+].[OH-:38].[NH4+:39]>C(O)C.O>[N:6]#[N:7].[C:8]([C@@H:11]([NH:20][C@H:21]([C:33]([N:39]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:8]([OH:10])=[O:38])=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([OH:10])=[O:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To 10 ml of 6NB sulfuric acid was added 1 g of N2 -(1(S)-carbamyl-3-phenylpropyl)-N6 -trifluoroacetyl-L-lysine followed by stirring for 15 hours at 80° C., after cooling the mixture to 0° C., 50 ml of water was added thereto, and after adjusting the pH thereof to 5.5 with an aqueous solution of 2N sodium hydroxide and then adjusting the pH to 7.5 with 1 N ammonium hydroxide, the volatile matters were distilled off. To the residue formed was added to 10 ml of ethanol, insoluble inorganic salts were filtered away, and after concentrated the filtrate under reduced pressure, the residual solids were purified by LH-20 chromatography (methanol) to provide 632 mg of N2 -(1(S)-carboxy-3-phenylpropyl)-L-lysyl-L-proline as solids. The properties of the product coincided with those described in Journal of Pharmaceutical Science, 74, 352(1985).

Workup

temperatureafter cooling the mixture to 0° C.
distillationthe volatile matters were distilled off
customTo the residue formed
filtrationwere filtered away
concentrationafter concentrated the filtrate under reduced pressure
customthe residual solids were purified by LH-20 chromatography (methanol)

Sources & evidence

ORD record: ord-043bb8f3a58f4c17a67403ebfe30e59a
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05136044

Reaction notes

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