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. 2020 Jul 1;5(27):16959–16966. doi: 10.1021/acsomega.0c02387

Table 1. HPLC Relative Retention Times (RRT) of Selected Process Impurities and their Relative Percent Areas at Various Stages in the Development of the Direct Phosphorylation Reaction Using POCl3.

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entry condition pyrophosphate (10) RRT 0.58 psilocybin (6) RRT 1.0 RRT 1.9 psilocin (4) RRT 2.21 RRT 2.41
1 10 min post POCl3 addition 0.15 69.46a 9.27 1.9 2.08
2 1 h post POCl3 addition 0.10 74.12a 6.77 1.60 2.58
3 2.5 h post POCl3 addition 0.94 77.31a 0.99 0.45 2.23
4 24 h after quench 1.18 80.27 0.78 2.69 11.99
5 crude-isolated product 0.24 97.61 0.33 1.38 0.24
6 mother liquors from isolation 6.43 46.01 1.32 25.32 15.99
7 after MeOH reslurry 0.11 98.93 0.11 0.13 0.56
8 after 40 °C H2O reslurry (development scale) 0.04 99.86 ndb 0.10 nd
9 after 40 °C H2O reslurry dried product (kilo-scale) 0.11 99.55 nd 0.11 nd
a

Indirect indication of formation of 7 by microquench of the aliquot prior to HPLC analysis.

b

Not detected.