Hydrochloric Acid → HCID 131713676, compound

HRID 485186Notes

Reaction equation

HRID 485186 reaction equation
[C:1]([NH:9][CH:10]([CH2:44][CH2:45][CH2:46][CH2:47][NH:48]C(OCC1C=CC=CC=1)=O)[C:11](=[O:43])[CH2:12][N:13](C(OCC1C=CC=CC=1)=O)[C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22]CC1C=CC=CC=1)=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:59].Cl.NCCCCC(NC(=O)C1C=CC=CC=1)C(=O)CN[C@H](C(N1CCC[C@H]1C(O)=O)=O)C.CO>C(O)C.[Pd].C(O)CCC.C(O)(=O)C.O>[ClH:59].[ClH:59].[NH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11](=[O:43])[CH2:12][NH:13][C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131713677HCID 131713677, compoundHCID 131713678HCID 131713678, compound

Product 1

HCID 131713676HCID 131713676, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 22056973Butanol acetic acid waterSolvent

Procedure

1-[N-[3-(Benzoylamino)-7-[[(phenylmethoxy)carbonyl]amino]-2-oxoheptyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline, phenylmethyl ester (1.3 g., 1.6 mmole) is dissolved in ethanol (75 ml.) and aqueous hydrochloric acid (1N, 5 ml.). Palladium on carbon catalyst (10%, 450 mg.) is added and the mixture is hydrogenated at atmospheric pressure overnight. The catalyst is filtered off and the solution is evaporated in vacuo. The residue is dissolved in water and lyophilized. The lyophilate is triturated with ether to give 0.6 g. of 1-[N-[7-amino-3-(benzoylamino)-2-oxoheptyl]-L-alanyl]-L-proline, hydrochloride; m.p. 80°-155°; [α]D22 =-50° (c=1.1, methanol). Rf 0.09 (silica gel, n-butanol/acetic acid/water, 4:1:1).

Workup

  1. customis hydrogenated at atmospheric pressure overnight
  2. filtrationThe catalyst is filtered off
  3. customthe solution is evaporated in vacuo
  4. dissolutionThe residue is dissolved in water
  5. customThe lyophilate is triturated with ether
  6. customto give 0.6 g

Sources & evidence

ORD record
ord-638d9cfd098841df9ea8045a7fa638a4
Source dataset
uspto-grants-1985_08
Patent number
US04535176

Reaction notes

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