HCID 86628895, compound → HCID 25225741, compound

HRID 1919422Notes

Reaction equation

HRID 1919422 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:38])([CH3:37])[C@@H:14]([O:29]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][O:19][C:20](=[O:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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]([CH3:38])([CH3:37])[C@@H:14]([OH:29])[C:15]([O:17][CH2:18][O:19][C:20](=[O:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86628895HCID 86628895, compound

Product 1

HCID 25225741HCID 25225741, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (2-phenylacetyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (28c) (60 mg, 0.11 mmol) and 60 mg of 10 wt.-% of palladium on activated carbon in 2 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 10 mg (20% yield) of the title compound (28) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.91 (s, 3H), 1.00 (s, 3H), 1.98 (s, 3H), 2.03-2.10 (m, 2H), 3.10-3.23 (m, 2H), 3.26 (br., 1H), 3.32-3.45 (m, 2H), 3.70 (s, 2H), 3.90 (d, J=9.6 Hz, 1H), 4.07 (s, 1H), 4.10 (d, J=9.2 Hz, 1H), 5.79 (d, J=5.6 Hz, 1H), 5.85 (br. m, 1H), 5.93 (d, J=5.6 Hz, 1H) 7.26-7.35 (m, 5H) ppm. MS (ESI) m/z: 460.05 (M+H)+, 481.99 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-df7a0b8ed68649688307f095fe0c4230
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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