Diethyl benzylphosphonate → HCID 69085438, compound

HRID 2362338Notes

Reaction equation

HRID 2362338 reaction equation
BrC1N=C([C@@H]([NH:17][C:18](=[O:24])[O:19]C(C)(C)C)[C@H](O)C2C=CC=CC=2)C=CC=1.[Br:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([CH:33]=1)[CH:31]=O.C(OP([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=O)OCC)C>>[Br:25][C:26]1[CH:33]=[C:30]([C@@H:31]2[C@@H:42]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:24][C:18](=[O:19])[NH:17]2)[CH:29]=[N:28][CH:27]=1

Participants

4

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 86673407HCID 86673407, compound

Product 1

HCID 69085438HCID 69085438, compound

Procedure

Prepared according to the same procedure as (±)-tert-Butyl (1R,2R)-1-(6-bromopyridin-2-yl)-2-hydroxy-2-phenylethylcarbamate, starting with 5-bromonicotinaldehyde and diethylbenzylphosphonate. 1H-NMR (CDCl3, 500 MHz) δ 8.67 (d, J=2.1 Hz, 1H), 8.37 (d, J=1.5 Hz, 1H), 7.91 (t, J=2.1 Hz, 1H), 7.43 (m, 3H), 7.30 (m, 2H), 7.12 (bs, 1H), 5.25 (d, J=7.6 Hz, 1H), 4.84 (d, J=7.6 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ ppm 159.0, 151.6, 146.4, 136.7, 136.4, 136.1, 129.7, 129.3, 126.1, 125.5, 121.6, 85.7, 62.3, 60.5. Mass spec.: 320.95 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3fc53f74c5e24b36bb2203b2d8da6676
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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