HCID 123320620, compound → HCID 123953362, compound

HRID 1776096Notes

Reaction equation

HRID 1776096 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C@@H:16]([C@@H:22]([O:35][Si:36]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])[C@@H:23]([O:25]CC1C=CC(OC)=CC=1)[CH3:24])[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C@@H:16]([C@@H:22]([O:35][Si:36]([CH:37]([CH3:39])[CH3:38])([CH:40]([CH3:42])[CH3:41])[CH:43]([CH3:45])[CH3:44])[C@@H:23]([OH:25])[CH3:24])[CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 123320620HCID 123320620, compound

Product 1

HCID 123953362HCID 123953362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(2S,6R)-2-((tert-Butoxycarbonyl)amino)-6-((1R,2S)-2-((4-methoxybenzyl)oxy)-1-((triisopropylsilyl)oxy)propyl)-9-methyldecanoic acid (8.55 g, 13.1 mmol) was dissolved in THF (40 ml) in a high pressure reactor with a stir bar. To the resulting solution was added 5% Pd/C (1.40 g, 0.656 mmol) was added, the reactor was sealed and purged with H2 (4×), and then charged to 600 psi with H2 at room temperature. The reactor was heated to 50° C. for 12 h and then stirred at room temperature overnight. The reaction mixture was filtered through a pad of Celite® and concentrated to yield the title compound as a colorless oil contaminated with 20% p-methoxytoluene (7.76 g, 89: 1H NMR (400 MHz, CDCl3) δ 5.05-4.92 (m, 1H), 4.37-4.22 (m, 1H), 3.89 (qd, J=6.4, 3.5 Hz, 1H), 3.83-3.78 (m, 1H), 1.93-1.77 (m, 2H), 1.74-1.45 (m, 5H), 1.45 (s, 9H), 1.45-1.19 (m, 2H), 1.19 (d, J=5.1 Hz, 3H), 1.14-1.02 (m, 24H), 0.87 (d, J=6.6 Hz, 6H); ESIMS m/z 554.5 ([M+Na]+).

Workup

  1. additionwas added
  2. customthe reactor was sealed
  3. custompurged with H2 (4×)
  4. additioncharged to 600 psi with H2 at room temperature
  5. filtrationThe reaction mixture was filtered through a pad of Celite®
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37e4c467b3d84589bc1f304c1e5e94e0
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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