HCID 86628920, compound → HCID 25225926, compound

HRID 1919451Notes

Reaction equation

HRID 1919451 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:44])([CH3:43])[C@@H:14]([O:35]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:34])[C:22]([CH3:33])([CH3:32])[CH2:23][O:24]CC1C=CC=CC=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>[Pd].CO>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:44])([CH3:43])[C@@H:14]([OH:35])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:34])[C:22]([CH3:32])([CH3:33])[CH2:23][OH:24])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86628920HCID 86628920, compound

Product 1

HCID 25225926HCID 25225926, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of [2,2-dimethyl-3-(phenylmethoxy)propanoyloxy]ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (46c) (0.13 g, 0.21 mmol) and 75 mg of 10 wt.-% of palladium on activated carbon in 6 mL of methanol (MeOH) was stirred overnight under a hydrogen atmosphere. After work-up and further purification by mass-guided preparative HPLC, 24 mg (25% yield) of the title compound (46) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3, both diastereomers): δ=0.96-0.99 (2s, 3H), 1.10-1.11 (2s, 3H), 1.18 (s, 3H), 1.20-1.21 (2s, 3H), 1.55-1.57 (2d, J=5.2, 5.6 Hz, 3H), 1.98-1.99 (2s, 3H), 2.03-2.12 (m, 2H), 2.54-2.68 (br. m, 1H), 3.11-3.29 (m, 2H), 3.30-3.51 (m, 3H), 3.51-3.63 (m, 2H), 3.93-3.96 (2d, J=8.8, 9.2 Hz, 1H), 4.05-4.07 (m, 1H), 4.14-4.17 (2d, J=9.6, 9.6 Hz, 1H), 5.92-5.98 (br. m, 1H), 6.91-6.98 (m, 1H) ppm. MS (ESI) m/z: 456.07 (M+H)+, 478.02 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter work-up and further purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-7854d6ba46de4d61b8a2f5319aa6fda8
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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