Ethanol → HCID 13454589, compound

HRID 1284946Notes

Reaction equation

HRID 1284946 reaction equation
C(O)C.Cl.C([N:12]([C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([OH:30])=[O:29])[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=2[S:21][CH2:20]1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])C1C=CC=CC=1>[C].[Pd].C(OCC)(=O)C>[CH2:17]([O:16][C:14]([CH2:13][NH:12][C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([OH:30])=[O:29])[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=2[S:21][CH2:20]1)=[O:15])[CH3:18]

Participants

5

Reactant 2

HCID 702EthanolHCID 70456751HCID 70456751, compound

Product 1

HCID 13454589HCID 13454589, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20 ml of ethanol and 0.5 g of 3(R)-(N-benzyl-N-ethoxycarbonylmethylamino)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid hydrochloride obtained in Reference Example 35 is catalytic reduction over 0.5 g of 10% palladium-carbon (containing 50% of moisture) as a catalyst at ordinary temperature and at atmospheric pressure. After the absorption of hydrogen stops, the catalyst is filtered off, and the filtrate is concentrated to give crystals. Ethyl acetate is added to the crystals, and the deposited substance are collected by filtration to yield 0.3 g of 3(R)-ethoxycarbonylmethylamino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as colorless prisms, m.p. 223°-226° C.

Workup

  1. customobtained in Reference Example 35
  2. customAfter the absorption of hydrogen
  3. filtrationthe catalyst is filtered off
  4. concentrationthe filtrate is concentrated
  5. customto give crystals
  6. filtrationthe deposited substance are collected by filtration

Sources & evidence

ORD record
ord-4aa70496d1c04d1fadc89f9115fd2c36
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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