HCID 53825676, compound → HCID 53709206, compound

HRID 1583817Notes

Reaction equation

HRID 1583817 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[O:17][C@@H:6]1[S:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[O:17][C@@H:6]1[S:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 53825676HCID 53825676, compound

Product 1

HCID 53709206HCID 53709206, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 (800 mg) in ethyl acetate (10 ml) and acetic acid (10 μl) containing 10% palladium-on-charcoal (400 mg) is hydrogenated overnight at room temperature. The catalyst is filtered off and washed with ethyl acetate. The combined filtrates are evaporated in vacuo to give 6 (780 mg, 97%); m.p. 73°-74° C. (ethyl ether-petroleum ether); [α]D27 +86.0±0.9° (C 1.08, chloroform).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with ethyl acetate
  3. customThe combined filtrates are evaporated in vacuo

Sources & evidence

ORD record
ord-93d5c07b4654464a9a5d21bcc49f1ca1
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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