HCID 68719474, compound → HCID 11995893, compound

HRID 2246704Notes

Reaction equation

HRID 2246704 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH2:7][O:8][P:9]([CH2:18][CH:19]([OH:32])[CH2:20][NH:21]C(OCC1C=CC=CC=1)=O)([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])=[O:5])[CH3:2]>C(O)C.[H][H].[Pd]>[CH2:1]([O:3][C:4]([O:6][CH2:7][O:8][P:9]([CH2:18][C@H:19]([OH:32])[CH2:20][NH2:21])([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 68719474HCID 68719474, compound

Product 1

HCID 11995893HCID 11995893, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

(3-Benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid ethoxycarbonyloxymethyl ester (0.263 g, 0.56 mmol) was dissolved in absolute ethanol (28 mL) and hydrogenated at RT via a hydrogen Paar shaker for 1 h at 55 psi with 10% Pd/C (0.127 g). The reaction mixture was filtered through celite and concentrated in vacuo to yield the title compound (187 mg, 0.56 mmol) as a foamy white solid. 1H NMR (CDCl3, 300 MHz): 7.90 (bs, 2H), 5.69 (m, 2H), 4.51 (bs, 1H), 4.23 (q, 2H), 3.27 (m, 1H), 3.17 (m, 1H), 2.20 (m, 2H), 1.88-1.64 (m, 8H), 1.34-1.00 (m, 6H), 1.32 (t, 3H). 31P NMR (CDCl3, 300 MHz): 61.14, 59.63. LC/MS m/z: [M+H]+=338.

Workup

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

Sources & evidence

ORD record
ord-7571975d22094be28bd1d553b71a2f21
Source dataset
uspto-grants-2010_03
Patent number
US07687540B2

Reaction notes

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