Diethyl phosphonomethanol → HCID 86619968, compound

HRID 1175672Notes

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:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH2:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:33][CH2:34][O:35][P:36]([O:40][CH2:41][CH3:42])([CH2:38][OH:39])=[O:37].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClC(Cl)C>[NH2:32][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[C:29]=1[N:30]=[CH:31][N:23]2[C@@H:10]1[O:11][C@:12]([CH3:22])([O:39][CH2:38][P:36](=[O:37])([O:40][CH2:41][CH3:42])[O:35][CH2:34][CH3:33])[C@@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@H:9]1[O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of compound 31.2 (280 mg, 0.59 mmol) in dichloroethane (5 mL) was added diethyl (hydroxymethyl) phosphonate (0.22 mL, 1.47 mmol) and pyridinium p-toluene sulfonate (56 mg, 0.29 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 31.3 (102 mg, 16% yield). 1H NMR (300 MHz, CDCl3): δ −0.45 (s, 3H), −0.08 (s, 3H), 0.05 (s, 3H), 0.71 (s, 9H), 0.98 (s, 9H), 1.35 (m, 6H), 1.61 (s, 3H), 3.78 (t, 1H), 3.95 (t, 1H), 4.04 (s, 1H), 4.21 (m, 4H), 4.96 (m, 1H), 6.24 (d, 1H, J=6.7), 8.10 (s, 1H), 8.70 (s, 1H). LRMS (ESI) MH+ C27H52N5O7PSi2 requires 646.9. Found 645.9.

Workup

concentrationconcentrated under reduced pressure
washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-60fb273135d54d2b9a89c78d2a2c407e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842672B2

Reaction notes

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