HCID 53656130, compound → HCID 54418104, compound

HRID 725607Notes

Reaction equation

HRID 725607 reaction equation
[CH2:1]([NH:5][C:6](=[O:47])[C@H:7]([CH3:46])[CH2:8][C@H:9]([OH:45])[C@@H:10]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:11][C@@H:12]([CH:34]([CH3:36])[CH3:35])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20]CC2C=CC=CC=2)=[C:16]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([NH:5][C:6](=[O:47])[C@H:7]([CH3:46])[CH2:8][C@H:9]([OH:45])[C@@H:10]([NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:11][C@@H:12]([CH:34]([CH3:35])[CH3:36])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 53656130HCID 53656130, compound

Product 1

HCID 54418104HCID 54418104, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.34 g of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-benzyloxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-butyl)-amide are hydrogenated in the presence of 400 mg of 5% Pd/C in 50 ml of methanol for 10 minutes at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by means of FC (50 g of silica gel, hexane/ethyl acetate=1:1). The title compound is obtained: Rf (hexane/ethyl acetate=1:1)=0.16; HPLC Rt =17.42 minutes; FAB-MS: (M+H)+ =567.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified by means of FC (50 g of silica gel, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-684cb2800eb34548bfc37757bbad3ed7
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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