(2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester → (2S, 9R)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt

HRID 1741436Notes

Reaction equation

HRID 1741436 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:8][CH2:9][CH2:10][CH2:11][N:12](CC1C=CC=CC=1)[CH2:13][C@H:14]([OH:18])[CH2:15][C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.O=[Pt]=O>[C:6]([OH:34])(=[O:5])[CH3:7].[C:6]([OH:34])(=[O:5])[CH3:7].[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C@H:14]([OH:18])[CH2:15][CH2:16][NH2:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 10695903(2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 131721417(2S, 9R)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate SaltYield 280.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

The Nε benzyl nitrile (6) (4.80 g, 10.7 mmol) was dissolved in glacial acetic acid (100 ml); 10% Pd--C (0.50 g) and PtO2 (1.00 g) were added; and hydrogen gas was introduced. The reaction was complete after 6 hours, and the catalyst was filtered through a bed of Celite and washed with acetic acid. The filtrate was concentrated in vacuo. Azeotropic removal of the acetic acid with toluene gave (7) as a colorless oil (5.10 g, 99%) 1H NMR (500 MHz) (CD3OD) δ4.02-3.94 (m, 2H), 3.14-2.86 (m, 6H), 1.94 (s, 6H), 1.87-1.58 (m, 8H), 1.46 (s, 9H), 1.44 (s, 9H). 13C NMR (CD3OD) δ169.6, 156.54, 85.3, 70.2, 62.6, 56.6, 54.2, 53.9, 34.0, 31.1, 28.2, 26.3, 23.2. HRMS m/z calcd. for C19H40N3O5 390.2968, found 390.2977. [α]25D +0.6° (c=1.00, CH3OH).

Workup

  1. filtrationthe catalyst was filtered through a bed of Celite
  2. washwashed with acetic acid
  3. concentrationThe filtrate was concentrated in vacuo
  4. customAzeotropic removal of the acetic acid with toluene

Sources & evidence

ORD record
ord-3e012de326dd426e961b9dd3395b3074
Source dataset
uspto-grants-1999_10
Patent number
US05973113

Reaction notes

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