HCID 117982165, compound → HCID 117974546, compound

HRID 1776095Notes

Reaction equation

HRID 1776095 reaction equation
C([O:8][C@@H:9]([CH3:49])[C@H:10]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@@H:11]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)[CH2:12][CH2:13][CH2:14][C@H:15]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:16]([O:18]CC1C=CC=CC=1)=[O:17])C1C=CC=CC=1>[Pd].CCOC(C)=O>[C:30]([O:29][C:27]([NH:26][C@@H:15]([CH2:14][CH2:13][CH2:12][C@H:11]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=1)[C@@H:10]([O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@@H:9]([OH:8])[CH3:49])[C:16]([OH:18])=[O:17])=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 1

HCID 117982165HCID 117982165, compound

Product 1

HCID 117974546HCID 117974546, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 25 mL screw top vial was charged with (2S,6R,7R,8S)-benzyl 8-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-6-(4-methylbenzyl)-7-phenoxynonanoate (741 mg, 1.11 mmol), EtOAc (10 mL), and 10% Pd/C (61 mg, 0.057 mmol). The vial was sealed with a septum-cap, and the reaction was briefly degassed under high vacuum, and then repressurized under about 1 atmosphere of H2 (balloon pressure). This process was repeated 2×, and the reaction was stirred at room temperature under balloon pressure of hydrogen. After stirring for 19 h, the solids were removed by filtration through a pad of Celite®, rinsing with excess EtOAc. The filtrate was concentrated and then dried under high vaccuum to afford the title compound as a white solid (516 mg, 91%): mp 48-51° C.; 1H NMR (400 MHz, CDCl3) δ 7.30-7.17 (m, 2H), 7.09 (s, 4H), 6.97-6.83 (m, 3H), 6.69-6.02 (m, 2H), 5.00 (d, J=8.3 Hz, 1H), 4.33-3.96 (m, 3H), 3.03 (dd, J=13.8, 5.3 Hz, 1H), 2.49 (dd, J=13.9, 8.9 Hz, 1H), 2.33 (s, 3H), 2.19-2.08 (m, 1H), 1.78-1.62 (m, 1H), 1.59-1.15 (m, 17H); 13C NMR (101 MHz, CDCl3) δ 176.73, 159.43, 155.73, 138.03, 135.33, 129.57, 129.10, 129.06, 120.88, 115.85, 82.16, 80.24, 68.15, 53.26, 41.47, 35.46, 32.45, 29.53, 28.35, 22.51, 21.05, 20.01; ESIMS: m/z 486 ([M+H]+).

Workup

  1. customThe vial was sealed with a septum-cap
  2. customthe reaction was briefly degassed under high vacuum
  3. stirringAfter stirring for 19 h
  4. customthe solids were removed by filtration through a pad of Celite®
  5. washrinsing with excess EtOAc
  6. concentrationThe filtrate was concentrated
  7. customdried under high vaccuum

Sources & evidence

ORD record
ord-bbfa1f430a1c49429349cdce7184f8f1
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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