HCID 131710175, compound → HCID 131710174, compound

HRID 1606835Notes

Reaction equation

HRID 1606835 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:24]([NH:26][C@H:27]([C:30]([NH:32][C@H:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH3:34])=[O:31])[CH2:28][OH:29])=[O:25])[CH2:15][CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]>[Pd].CO>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:24]([NH:26][C@H:27]([C:30]([NH:32][C@H:33]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH3:34])=[O:31])[CH2:28][OH:29])=[O:25])[CH2:15][CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:8])([CH3:7])[CH3:9]

Participants

4

Reactant 1

HCID 131710175HCID 131710175, compound

Product 1

HCID 131710174HCID 131710174, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 10.5 g. (14.5 mmoles) of Z-29-32-OtBu in 130 ml. of methanol is hydrogenated in the presence of 1 g. of palladium-on-carbon. When the reaction terminates, the catalyst is removed by filtration, and the filtrate is evaporated to dryness. The residue is triturated with petroleum ether. 8.35 g. (97.5 %) of H-29-32-OtBu are obtained. M.p.: 81-82°C; Rf11 = 0.1; [α]D = -24.3° (c = 1, in ethanol).

Workup

  1. customWhen the reaction terminates
  2. customthe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-907f1bb10ddc4bab9206198f70fc29f1
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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