Methanol → HCID 25225745, compound

HRID 1919449Notes

Reaction equation

HRID 1919449 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:41])([CH3:40])[C@@H:14]([O:32]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:31])[CH2:22][O:23]CC1C=CC=CC=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2].CO>[Pd].C(OCC)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:41])([CH3:40])[C@@H:14]([OH:32])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:31])[CH2:22][OH:23])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 86628917HCID 86628917, compound

Product 1

HCID 25225745HCID 25225745, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of [2-(phenylmethoxy)acetyloxy]ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (45a) (0.10 g, 0.17 mmol) and 0.1 g of 10 wt.-% of palladium on activated carbon in 6 mL of a mixture of methanol (MeOH) and ethyl acetate (EtOAc) was stirred overnight under a hydrogen atmosphere. After work-up and further purification by mass-guided preparative HPLC, 51 mg (73% yield) of the title compound (45) was obtained as a colorless, viscous oil after lyophilization of the solvents. 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.02-1.05 (2s, 3H), 1.10-1.13 (2s, 3H), 1.60 (t, J=5.2 Hz, 3H), 2.01 (s, 3H), 2.05-2.12 (m, 2H), 2.84-3.03 (br. m, 1H), 3.14-3.26 (m, 2H), 3.34-3.46 (m, 2H), 3.97-4.16 (m, 3H), 4.22 (s, 2H), 5.56-5.96 (br. m, 1H), 7.00-7.08 (m, 1H) ppm. MS (ESI) m/z: 414.02 (M+H)+, 435.96 (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-79562eb293c24d8b8d28691f4153c544
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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