Hydrochloric Acid → HCID 69637283, compound

HRID 431514Notes

Reaction equation

HRID 431514 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH:4]=[CH:5][C:6]1[S:7][C:8]([C:11](=[O:33])[NH:12][CH2:13][C@H:14]([NH:22]C(OCC2C=CC=CC=2)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:10]=1.[ClH:35]>CO.[Pd]>[ClH:35].[C:18]([O:17][C:15](=[O:16])[C@@H:14]([NH2:22])[CH2:13][NH:12][C:11]([C:8]1[S:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:34])=[CH:10][CH:9]=1)=[O:33])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 57221728HCID 57221728, compound

Product 1

HCID 69637283HCID 69637283, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent3×

Procedure

6.85 g of 3-(5-(((2S)-2-benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-acrylic acid methyl ester (example 3, step a) were dissolved in 220 ml of methanol. 1.3 g of 10% palladium on charcoal and 2.8 ml of a 5N solution of hydrogen chloride in methanol were added and the hydrogenation was started. After 6 hours the pH was adjusted with 5N solution of hydrogen chloride in methanol to 3.5, and further 0.6 g of the catalyst were added. After 14 hours the hydrogenation was complete. The catalyst was removed by filtration. After standard work-up 4.88 g of the title compound were obtained.

Workup

  1. additionwere added
  2. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-8c4e5df137f74804ba1511b5ffd337d9
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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