HCID 25218255, compound → HCID 25218381, compound

HRID 1671449Notes

Reaction equation

HRID 1671449 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([OH:25])[C:15]([O:17]CC1C=CC=CC=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:27])([CH3:26])[C@@H:14]([OH:25])[C:15]([OH:17])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 25218255HCID 25218255, compound

Product 1

HCID 25218381HCID 25218381, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of phenylmethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-2-hydroxy-3,3-dimethylbutanoate (31) (40 mg, 0.1 mmol) and 30 mg of 10 wt-% palladium on activated carbon in 2 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After filtration through a 0.2 μM nylon syringe filter and evaporation of the solvents, 6.7 mg (23% yield) of the title compound (33) was obtained as a pale-yellow, viscous oil. 1H NMR (400 MHz, DMSO-d6): δ=0.90 (s, 3H), 0.91 (s, 3H), 1.80 (s, 3H), 1.76-1.85 (m, 2H), 3.09-3.16 (m, 2H), 3.28-3.35 (m, 2H, superimposed with residual water), 3.76-3.82 (br. m, 1H), 3.94 (d, J=8.8 Hz, 1H), 4.07 (d, J=8.8 Hz, 1H), 7.90 (br. t, J=5.2 Hz, 1H), 12.59 (br. s, 1H) ppm. MS (ESI) m/z: 312.0 (M+H)+, 334.0 (M+Na)+, 310.1 (M−H)−. The analytical data was consistent with the proposed structure.

Workup

  1. filtrationAfter filtration through a 0.2 μM nylon syringe
  2. filtrationfilter
  3. customevaporation of the solvents

Sources & evidence

ORD record
ord-2bb9b5413391492aa93613e7e9096d69
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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