HCID 49797468, compound → HCID 9820646, compound

HRID 1671749Notes

Reaction equation

HRID 1671749 reaction equation
C1C=CN=CC=1.[CH:7]1[C:8]2[C:21]3=[CH:22][C@H:23]([OH:31])[C@H:24]4[O:29][P:27]([OH:30])(=[O:28])[O:26][C@H:25]4[C@@H:20]3[NH:19][C:17](=[O:18])[C:9]=2[C:10]([OH:16])=[C:11]2[O:15][CH2:14][O:13][C:12]=12.[H][H]>O>[CH:7]1[C:8]2[C:21]3=[CH:22][C@H:23]([OH:31])[C@H:24]4[O:29][P:27]([OH:30])(=[O:28])[O:26][C@H:25]4[C@@H:20]3[NH:19][C:17](=[O:18])[C:9]=2[C:10]([OH:16])=[C:11]2[O:15][CH2:14][O:13][C:12]=12

Participants

4

Reactant 2

HCID 49797468HCID 49797468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9820646HCID 9820646, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of pyridinium narcistatin (3a, 0.05 g) in water (2 ml) was obtained by heating (water bath) at 60° C. The solution was allowed to cool prior to passing through a column prepared from Dowex 50X8-200 cation exchange resin (hydrogen form). A suspension began to form in the column as the phosphoric acid (3b) formed. The column was eluted with water and phosphoric acid 3b eluted as a milky white suspension. The combined fractions containing phosphoric acid 3b were freeze dried to afford the product as a colorless solid, (36 mg, 86%); m.p. 175° C. (dec.); 1H NMR (DMSO-d6, 300 MHz), δ 13.65 (s, 1H), 9.02 (s, 1H), 7.06 (s, 1H), 6.48 (s, 1H), 6.17 (d, Jab=10.2 Hz, 1H), 6.06 (m, 2H), 4.46-4.30 (m, 3H), 4.18 (m, 1H); calc for C14H13NO9P 370.0328; found by HR (APCI) [M+H]+ 370.0361.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-8432a2c4012f4b6ea53a6f043ccbd5a2
Source dataset
uspto-grants-2011_08
Patent number
US07994320B2

Reaction notes

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