Methanol → HCID 10155964, compound

HRID 2304991Notes

Reaction equation

HRID 2304991 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][C:11]([NH:29]C(OCC1C=CC=CC=1)=O)([CH3:28])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)(=[O:8])[O:5]CC)C.CO>C(Cl)Cl>[NH2:29][C:11]([CH3:28])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)[CH2:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 86585468HCID 86585468, compound

Product 1

HCID 10155964HCID 10155964, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-diethyl 3-benzyloxycarbonylamino-3-methyl-5-(4-(octyl)phenyl)pentylphosphonic acid (0.097 g, 0.173 mmol) in methylene chloride (1 ml) was added aodotrimethylsilane (0.100 ml, 0.690 mmol). After stirring for 1 h, methanol was added (1 ml) and the reaction was concentrated. HPLC purification (YMC-Pack pro C18, 150×20 mm, acetonitrile/water+0.1% TFA 10/90 to 0/100 over 15 minutes, 20 ml/min, 254 nM) yielded a waxy solid (0.051 g): 1H NMR (500 MHz , CDCl3): δ7.09-7.14 (m, 4H), 2.64 (t, J=8.7 Hz, 2H), 2.56 (t, J=7.7 Hz, 3H), 1.98-2.02 (m, 2H), 1.88-1.92 (m, 2H), 1.75-1.82 (m, 2H), 1.56-1.59 (m, 2H), 1.39 (s, 3H), 1.24-1.34 (m, 12H), 0.89 (t, J=6.89 Hz, 3H); MS m/e 370.3 (M+).

Workup

  1. concentrationthe reaction was concentrated
  2. customHPLC purification (YMC-Pack pro C18, 150×20 mm, acetonitrile/water+0.1% TFA 10/90 to 0/100 over 15 minutes, 20 ml/min, 254 nM)

Sources & evidence

ORD record
ord-0c03ef641c9a4b22a1e50a4befca26c8
Source dataset
uspto-grants-2002_08
Patent number
US06437165B1

Reaction notes

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