HCID 178418361, compound → HCID 178447520, compound

HRID 2246702Notes

Reaction equation

HRID 2246702 reaction equation
C(OC([NH:11][CH2:12][C@H:13]([OH:33])[CH2:14][C:15]([O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[O:16][PH2:17]=[O:18])=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:11][CH2:12][C@H:13]([OH:33])[CH2:14][C:15]([O:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:30])[CH3:31])([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[O:16][PH2:17]=[O:18]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178447519HCID 178447519, compound

Product 1

HCID 178447520HCID 178447520, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,2-Dimethyl-propionic acid ((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinoyloxymethyl ester (0.90 g, 0.39 mmol) was dissolved in ethanol (35 mL) and was hydrogenated via a hydrogen par shaker for 3 h at 50 psi with 10% Pd/C (0.09 g) as a catalyst. The reaction was filtered through celite and concentrated in vacuo to give 2,2-dimethyl-propionic acid ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinoyloxymethyl ester (130 mg, 0.37 mmol). 1H NMR (CDCl3, 300 MHz): δ 5.65 (m, 1H), 4.2 (m, 1H), 3.8 (m, 1H), 3.60 (m, 1H), 2.01-1.55 (m, 14H), 1.40-0.95 (m, 11H). 31P NMR (CDCl3, 300 MHz): 60.65, 59.20. LC/MS m/z: [M+H]+=350.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3fed5b726a84306b87bf3140a9c4d8c
Source dataset
uspto-grants-2010_03
Patent number
US07687540B2

Reaction notes

Loading…