HCID 86726828, compound → HCID 86726827, compound

HRID 1499609Notes

Reaction equation

HRID 1499609 reaction equation
[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:35]([O-])=O)[C:13]([N:14]3[CH2:19][C@H:18]([CH:20]4[CH2:22][CH2:21]4)[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@H:16]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]>CO.CCOC(C)=O>[C:24]([O:23][C@@H:17]1[C@@H:18]([CH:20]2[CH2:21][CH2:22]2)[CH2:19][N:14]([C:13]2[C:12]([NH2:35])=[CH:11][N:10]=[C:9]3[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7][C:8]=23)[CH2:15][C@H:16]1[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:26])[CH3:25]

Participants

4

Reactant 1

HCID 86726828HCID 86726828, compound

Product 1

HCID 86726827HCID 86726827, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{(3R,4R,5S)-4-(acetyloxy)-3-[(tert-butoxycarbonyl)amino]-5-cyclopropylpiperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (0.055 g, 0.11 mmol) in MeOH (5.0 mL) and EtOAc (1.0 mL) was deoxygenated and purged with nitrogen prior to the addition of 10% palladium (dry basis) on activated carbon (wet, Degussa type E101 NE/W) (0.025 g). The reaction mixture was stirred under an atmosphere of hydrogen, introduced via a balloon, for 2 h. The crude reaction mixture was filtered through a pad of diatomaceous earth and the solids were washed thoroughly with EtOAc and MeOH. The filtrate was concentrated under reduced pressure to afford the sub-title compound (0.052 g, 100%). LCMS (ESI) m/z calc. for C25H37N4O6 489.3 [M+H]+. found 489.0.

Workup

  1. custompurged with nitrogen
  2. additionto the addition of 10% palladium (dry basis) on activated carbon (wet, Degussa type E101 NE/W) (0.025 g)
  3. additionintroduced via a balloon, for 2 h
  4. customThe crude reaction mixture
  5. filtrationwas filtered through a pad of diatomaceous earth
  6. washthe solids were washed thoroughly with EtOAc and MeOH
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d17f9ad824d040b09ad19641fe7bb15c
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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