Hydrochloric Acid → Boc-Arg-Pro-Gly-Pro

HRID 1481659Notes

Reaction equation

HRID 1481659 reaction equation
[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:13]([N:15]1[CH2:40][CH2:39][CH2:38][C@H:16]1[C:17]([NH:19][CH2:20][C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([O:27]CC1C=CC=CC=1)=[O:26])=[O:22])=[O:18])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:12])[NH:8][N+]([O-])=O.Cl.[O-2].[Al+3].[O-2].[O-2].[Al+3].[H][H]>CO.[Pd]=O>[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:13]([N:15]1[CH2:40][CH2:39][CH2:38][C@H:16]1[C:17]([NH:19][CH2:20][C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([OH:27])=[O:26])=[O:22])=[O:18])=[O:14])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9989226AluminaHCID 178418361HCID 178418361, compoundHCID 178454198HCID 178454198, compound

Product 1

HCID 178454179Boc-Arg-Pro-Gly-Pro

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 887MethanolSolvent

Procedure

4.76 g (6.5 mmol) of Boc-Arg(NO2)-Pro-Gly-Pro-OBzl were dissolved in 100 ml of methanol; then 1 ml 1N hydrochloric acid and 4.67 g of catalyst, viz. 10% palladium oxide on neutral aluminum oxide, were added, and hydrogenation in the stream of dry hydrogen at room temperature under 1 atm. was conducted for 6 hours. Then, the catalyst was filtered off and washed on the filter with methanol. Pooled filtrate was evaporated to dryness. The residue was precipitated with ether from the absolute methanol. Then, it was dried under vacuum, while desiccant was changed several times.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. washwashed on the
  3. filtrationfilter with methanol
  4. customPooled filtrate was evaporated to dryness
  5. customThe residue was precipitated with ether from the absolute methanol
  6. customThen, it was dried under vacuum, while desiccant

Sources & evidence

ORD record
ord-d218e8570c15437fbadbccebceee5807
Source dataset
uspto-grants-2016_08
Patent number
US09409947B2

Reaction notes

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