(S)-benzyl 7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylate → HCID 58313066, compound

HRID 79909Notes

Reaction equation

HRID 79909 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:28]([CH3:30])[CH3:29])[C:7]([N:9]1[C@H:17]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)=[O:8])=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:28]([CH3:30])[CH3:29])[C:7]([N:9]1[C@H:17]([C:18]([OH:20])=[O:19])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 59611049(S)-benzyl 7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylate

Product 1

HCID 58313066HCID 58313066, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-benzyl 7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylate (2.3 g, 5.47 mmol) was dissolved in ethyl alcohol (55 mL) and under Argon charged with 10% Pd/C in a round bottom flask. The flask was then sealed with a rubber septa and the air was removed by vacuum and replaced with H2 from a balloon. This process repeated three times and the mixture was stirred under H2 atmosphere for 18 hours. The resulting mixture was then passed through a elite plug and concentrated down on rotovap to yield 1.76 g, 98% desired product.

Workup

  1. customThe flask was then sealed with a rubber septa
  2. customthe air was removed by vacuum
  3. concentrationconcentrated down on rotovap

Sources & evidence

ORD record
ord-1c6c21aee5514327bfb2dabb0a133868
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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