HCID 57978218, compound → HCID 57978258, compound

HRID 1866522Notes

Reaction equation

HRID 1866522 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:31])[CH2:16][NH:17][C@H:18]([CH3:30])[CH2:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:11][C:10]=1[CH2:32][OH:33])C1C=CC=CC=1>[Pd].C(O)C>[NH3:17].[OH:31][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:32][OH:33])[CH:11]=1)[CH2:16][NH:17][C@H:18]([CH3:30])[CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 1

HCID 57978218HCID 57978218, compound

Product 2

HCID 222AmmoniaHCID 57978258HCID 57978258, compoundYield 187.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of methyl 3-[(2R)-2-({(2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-hydroxyethyl}amino)propyl]benzoate (Preparation 61) (6.83 g, 15.2 mmol) and 10% palladium on carbon (683 mg) in ethanol (100 ml) was stirred under an atmosphere of hydrogen (60 psi) at room temperature for 18 hours. The catalyst was filtered off through arbocel and the filtrate concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95:5:0.5 changing to 90:10:1, by volume) to give the title compound as a pale yellow gum (5.12 g). 1H NMR (400 MHz, CD3OD): δ=7.85-7.83 (1H, m), 7.79 (1H, s), 7.36-7.35 (2H, m), 7.20 (1H, s), 7.02-6.99 (1H, dd), 6.68-6.65 (1H, d), 4.61-4.58 (1H, m), 4.60 (2H, s), 3.90 (3H, s), 2.97-2.87 (2H, m), 2.80-2.62 (3H, m), 1.08-1.07 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 360, [M+Na]+ 382, [M−H]− 358.

Workup

  1. filtrationThe catalyst was filtered off through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-41620a75b96a446592addd6db198a5d9
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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