Diethyl phosphonomethanol → HCID 86619967, compound

HRID 1175669Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:12](=[CH2:22])[O:11][C@H:10]1[N:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[N:25][C:24]1=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:31][CH2:32][O:33][P:34]([O:38][CH2:39][CH3:40])([CH2:36][OH:37])=[O:35].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClC(Cl)C>[CH2:32]([O:33][P:34]([CH2:36][O:37][C@:12]1([CH3:22])[C@@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C@H:10]([N:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[N:25][C:24]2=[O:30])[O:11]1)(=[O:35])[O:38][CH2:39][CH3:40])[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of compound 30.3 (840 mg, 1.85 mmol) in dichloroethane (20 mL) was added diethyl (hydroxymethyl) phosphonate (0.41 mL, 2.87 mmol) and pyridinium p-toluene sulfonate (0.23 g, 0.92 mmol). The mixture was heated to 60° C. for 1 h and then concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10% MeOH in CH2Cl2 to give compound 30.4 (289 mg, 24% yield). 1H NMR (300 MHz, CDCl3): δ0.04 (s, 3H), 0.08 (s, 3H), 0.10 (s, 6H), 0.89 (s, 9H), 0.92 (s, 9H), 1.38 (m, 6H), 1.49 (s, 3H), 3.93 (m, 1H), 4.14 (m, 2H), 4.20 (m, 1H), 4.38 (m, 1H), 5.83 (d, 1H, J=7.7), 6.08 (d, 1H, J=4.0), 7.99 (d, 1H, J=7.3). LRMS (ESI) MH+ C26H52N3O8PSi2 requires 622.9. Found 622.1.

Workup

concentrationconcentrated under reduced pressure
washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-1b1f86774b934f1ba3c632cea7491906
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842672B2

Reaction notes

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