HCID 67104853, compound → HCID 67105482, compound

HRID 41337Notes

Reaction equation

HRID 41337 reaction equation
C([O:8][C:9]1[C:14]([CH:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C1C=CC=CC=1>[Pd].CCO>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][CH:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]=1[OH:8])[CH3:16]

Participants

4

Reactant 1

HCID 67104853HCID 67104853, compound

Product 1

HCID 67105482HCID 67105482, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 19 (1.9 g, 4.6 mmol), 20% Pd—C (˜55% H2O) and EtOH (50 mL) was hydrogenated at 20 psi H2 for 2 hr at which time LCMS show no 19 remained. The mixture was filtered through Celite, washing the Celite pad with EtOH (100 mL). The filtrate was concentrated under reduced pressure to give a yellow-green oil. The crude product was purified on an Analogic MPLC, eluting with a gradient of 0%-20% EtOAc/hexanes to give 0.9 g (60%) of D1 as a faintly yellow viscous oil. On lengthy standing (>2 months) D1 slowly crystallized as a white solid (mp 116.0-116.8° C.).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashing the Celite pad with EtOH (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a yellow-green oil
  5. customThe crude product was purified on an Analogic MPLC
  6. washeluting with a gradient of 0%-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-6faf17db3aa643bf908a4b00e00304e6
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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