Sodium Hydroxide → HCID 178503028, compound

HRID 1525285Notes

Reaction equation

OC1C(C(N[C@@H](C2C=CC=CC=2P(C)(=O)OCC)C2C=CC=CC=2)=O)=CN=C(N2C=CC=N2)N=1.[OH:35][C:36]1[C:41]([C:42]([NH:44][C@H:45]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:46]2[CH:47]=[C:48]([P:52]([CH3:57])(=[O:56])[O:53]CC)[CH:49]=[CH:50][CH:51]=2)=[O:43])=[CH:40][N:39]=[C:38]([N:64]2[CH:68]=[CH:67][CH:66]=[N:65]2)[N:37]=1.[OH-].[Na+]>O1CCOCC1>[OH:35][C:36]1[C:41]([C:42]([NH:44][C@H:45]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:46]2[CH:47]=[C:48]([P:52]([CH3:57])(=[O:53])[OH:56])[CH:49]=[CH:50][CH:51]=2)=[O:43])=[CH:40][N:39]=[C:38]([N:64]2[CH:68]=[CH:67][CH:66]=[N:65]2)[N:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl ((R)-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)(phenyl)methyl)phenyl(methyl)phosphinate, 24-f, (18.8 g, 390 mmol) was dissolved in 200 ml of dioxane and treated with 50 ml of 3N NaOH. The mixture was heated at 80° C. for one hour. The mixture was then concentrated under vacuum and the residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified with conc. HCl to pH=1 and the expected product crashed out, 24-1, (11 g of crude). The product can be further purified via prep-HPLC. 1H NMR (300 MHz, DMSO-d6): δ 8.63 (s, 1H), 8.44 (s, 1H), 8.07 (s, 1H), 7.50 (m, 2H), 7.38 (m, 7H), 6.73 (s, 1H), 6.35 (d, 1H), 1.53 (d, 3H). (M+H)+=450.1.

Workup

concentrationThe mixture was then concentrated under vacuum
additionthe residue was diluted with water
washwashed with ethyl acetate
customThe product can be further purified via prep-HPLC

Sources & evidence

ORD record: ord-c43e3228c08444f4b7b0bf0bb63983fd
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

Loading…