tert-butyl(1S)-5-{[(benzyloxy)carbonyl]amino}-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate → tert-butyl (1S)-5-amino-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate

HRID 1180744Notes

Reaction equation

HRID 1180744 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:17]([OH:29])[C:18](=[O:28])[NH:19][C@@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])=O)C1C=CC=CC=1.[H][H]>[Pd].O.C(O)C>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:17]([OH:29])[C:18](=[O:28])[NH:19][C@@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21]

Participants

6

Reactant 2

HCID 58979678tert-butyl(1S)-5-{[(benzyloxy)carbonyl]amino}-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 58979670tert-butyl (1S)-5-amino-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamateYield 93.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A slurry of 1.5 g of 10 wt % palladium on carbon in 3 mL of water was added to a solution of 15.28 g (29.70 mmol) of tert-butyl (1S)-5-{[(benzyloxy)carbonyl]amino}-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate in 200 mL of ethanol. The resulting slurry was stirred vigorously under 45 psi of hydrogen gas at 50° C. for 18 h. The catalyst was then filtered off, rinsing with 400 mL of ethanol. Concentration of the filtrate under vacuum afforded 10.52 g (93%) of tert-butyl (1S)-5-amino-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate as a colorless oil that crystallized upon standing under vacuum. 1H NMR (300 MHz, DMSO-d6) δ 8.15 (d, J=8 Hz) and 8.08 (d, J=8 Hz) total 1H; 7.90-7.87 (m, ca 1H); 7.87-7.28 (m, 4H); 7.25-7.20 (m, 1H); 6.51 (d, J=9 Hz) and 6.17 (d, J=9 Hz) total 1H; 4.99-4.92 (m, 1H); 3.96 (d, J=4 Hz) and 3.90 (d, J=3 Hz) total 1H; 3.80-3.69 (m, 1H); 2.68-2.64 (m) and 2.53-2.57 (m) total 1H; 1.53-1.23 (m, 18H). ES-LCMS m/z 380 (M+H).

Workup

  1. filtrationThe catalyst was then filtered off
  2. washrinsing with 400 mL of ethanol

Sources & evidence

ORD record
ord-99d54eb79e4549b9a340683d4884eb72
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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