Hydrochloric Acid → HCID 86753433, compound

HRID 1457589Notes

Reaction equation

HRID 1457589 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:25]=1[OH:36])[C:17]([O:19][CH3:20])=[O:18])=O)C1C=CC=CC=1.CO.[ClH:40]>[C].[Pd].CCCCCC>[ClH:40].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([C:32]([CH3:33])([CH3:34])[CH3:35])[C:25]=1[OH:36])[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86753430HCID 86753430, compound

Product 1

HCID 86753433HCID 86753433, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8058HexaneSolvent

Procedure

To a mixed solution comprising 1 g of 2-[3-((1S)-5-benzyloxycarbonylamino-1-methoxycarbonylpentyl)ureido]-4-methoxy-6-tert-butylphenol and 30 ml of methanol were added 0.5 ml of conc. hydrochloric acid and 200 mg of 10% palladium-carbon (Pd-C). The mixture was subjected to catalytic reduction at normal temperature under normal pressure for one hour. After removing the catalyst, the filtrate was condensed. Hexane was added to the residue to give 685 mg of 2-[3-((1S)-5-amino-1-methoxycarbonylpentyl)ureido]-4-methoxy-6-tert-butylphenol hydrochloride (yield: 85%, state: yellow powder, IR: 3300 (br), 1725, 1650, 1560 cm-1).

Workup

  1. customAfter removing the catalyst
  2. customcondensed

Sources & evidence

ORD record
ord-22019def4b054587bfdd1dda21852e81
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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