HCID 86638861, compound → HCID 67311547, compound

HRID 2065815Notes

Reaction equation

HRID 2065815 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]1[CH2:23][CH:22]1[C@@H:24]([NH:29]C(=O)OCC1C=CC=CC=1)[CH2:25][CH:26]([CH3:28])[CH3:27])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.CCOC(C)=O>[Si:1]([O:18][CH2:19][CH2:20][CH:21]1[CH2:23][CH:22]1[C@@H:24]([NH2:29])[CH2:25][CH:26]([CH3:27])[CH3:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86638861HCID 86638861, compound

Product 1

HCID 67311547HCID 67311547, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A flask containing a solution of the Cbz-protected amine 11b (460 mg, 0.846 mmol) in a 5:1 MeOH/EtOAc mixture (12 mL) was purged and filled 3 times with argon, then 10% Pd/C (50 mg) was added. The flask was purged and filled 3 times with H2, and the resulting black suspension was stirred at rt under H2 (1 atm). Since the reaction did not reach completion after 3 h, an additional amount of 10% Pd/C (30 mg) was added and stirring under H2 was continued for 5 h. The reaction mixture was then filtered through a pad of Celite, the Celite washed with MeOH and AcOEt, and the solution concentrated in vacuo to yield 317 mg (92%) of the crude title compound as a pale yellow oil, that was used for the next step without further purification.

Workup

  1. customwas purged
  2. additionfilled 3 times with argon
  3. addition10% Pd/C (50 mg) was added
  4. customThe flask was purged
  5. additionfilled 3 times with H2
  6. customafter 3 h
  7. additionan additional amount of 10% Pd/C (30 mg) was added
  8. stirringstirring under H2
  9. filtrationThe reaction mixture was then filtered through a pad of Celite
  10. washthe Celite washed with MeOH and AcOEt
  11. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-544d0c8b7f1a43bfa6e7906e08b20f06
Source dataset
uspto-grants-2012_10
Patent number
US08288551B2

Reaction notes

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