Ethanol → HCID 54343075, compound

HRID 2372595Notes

Reaction equation

HRID 2372595 reaction equation
C(O)C.C(O)(=O)C(O)=O.[C:10]([O:14][C:15](=[O:32])[CH2:16][N:17]([C:27](=[O:31])[C@H:28]([CH3:30])[NH2:29])[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)([CH3:13])([CH3:12])[CH3:11].C([O-])(=O)C.[Na+].C([O:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][C:54](=O)[C:55]([O:57][CH2:58][CH3:59])=[O:56])=[CH:48][CH:47]=1)C1C=CC=CC=1>[Ni].C(O)(=O)C>[C:10]([O:14][C:15](=[O:32])[CH2:16][N:17]([C:27](=[O:31])[C@H:28]([CH3:30])[NH:29][CH:54]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:53][CH2:52][C:49]1[CH:50]=[CH:51][C:46]([OH:45])=[CH:47][CH:48]=1)[CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 13132289HCID 13132289, compoundHCID 19903100HCID 19903100, compound

Product 1

HCID 54343075HCID 54343075, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

To 100 ml of ethanol, there are added 3 g of L-alanyl-N-(indan-2-yl)glycine tert-butyl ester oxalate, 0.75 g of sodium acetate, 1.5 g of acetic acid, 5 g of molecular sieve 3A and 5 g of ethyl 4-(4-benzyloxyphenyl)-2-oxobutyrate, and catalytic reduction is carried out using Raney nickel as catalyst. When the hydrogen absorption has ceased, the catalyst is removed, and catalytic reduction is further carried out using palladium-carbon as catalyst. The catalyst is filtered off and the solvent is distilled off under reduced pressure to give N-[1-ethoxycarbonyl-3-(p-hydroxyphenyl)propyl]L-alanyl-N-(indan-2-yl)glycine tert-butyl ester as oil. This oil is converted by the reaction procedure as used in Example 4 to N-[1-ethoxycarbonyl-3-(4-hydroxyphenyl)propyl]-L-alanyl-N-(indan-2-yl)glycine hydrobromide, which is further converted to the hydrochloride by the procedure of Example 6. There is thus obtained 0.65 g of N-[1-ethoxycarbonyl-3-(4-hydroxyphenyl)propyl]-L-alanyl-N-(indan-2yl)glycine hydrochloride as colorless crystals melting at 126°-130° C. with decomposition.

Workup

  1. customWhen the hydrogen absorption
  2. customthe catalyst is removed
  3. filtrationThe catalyst is filtered off
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-2691605d08b548aa9dbf0f968a88e9cd
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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