HCID 86618148, compound → HCID 68569637, compound

HRID 2246577Notes

Reaction equation

HRID 2246577 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:10][C@H:9]([N:11](CC2C=CC(OC)=CC=2)[CH3:12])[CH2:8][CH2:7][C@@H:6]1[N:22]1[CH2:26][CH2:25][C@H:24]([NH:27]C(=O)OCC2C=CC=CC=2)[C:23]1=[O:38])(=[O:3])[CH3:2]>CO.O[Pd]O>[NH2:27][C@H:24]1[CH2:25][CH2:26][N:22]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([NH:11][CH3:12])[CH2:10][C@H:5]2[NH:4][C:1](=[O:3])[CH3:2])[C:23]1=[O:38]

Participants

4

Reactant 1

HCID 86618148HCID 86618148, compound

Product 1

HCID 68569637HCID 68569637, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 178526213HCID 178526213, compoundCatalystHCID 887MethanolSolvent

Procedure

A sample of benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-((4-methoxybenzyl)(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (25.0 g, 47.8 mmol) was dissolved in MeOH. The flask was charged with dihydroxypalladium (6 g, 8.54 mmol), evacuated, and back filled with hydrogen from a hydrogen balloon. The mixture was stirred at RT overnight and then filtered (3×80 mL isopropanol washes). The residue was concentrated under high vacuum to dryness. The residue was dried azeotropically with iso-propanol (4×150 mL) under reduced pressure to afford N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(methylamino)cyclohexyl)acetamide (12.5 g, 46.6 mmol, 97% yield). LC/MS found [M+H]+=269.

Workup

  1. customevacuated
  2. additionback filled with hydrogen from a hydrogen balloon
  3. filtrationfiltered (3×80 mL isopropanol washes)
  4. concentrationThe residue was concentrated under high vacuum to dryness
  5. dry with materialThe residue was dried azeotropically with iso-propanol (4×150 mL) under reduced pressure

Sources & evidence

ORD record
ord-586c14b0ad14428d8cefaecc76ac51bd
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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