Sodium Hydroxide → HCID 178503027, compound

HRID 1525290Notes

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 ((S)-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamido)(phenyl)methyl)phenyl(methyl)phosphinate, 25-e, (33 g, 69 mmol) was dissolved in 400 ml of dioxane and treated with 100 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, 25-1, (11 g of crude). The product can be further purified via prep-HPLC. 1H NMR (300 MHz, DMSO-d6): δ 10.39 (br, 1H), 8.62 (s, 1H), 8.45 (s, 1H), 8.07 (s, 1H), 7.37 (m, 9H), 6.73 (s, 1H), 6.33 (d, 1H), 1.52 (d, 3H). (2M+H)+=899.0.

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-c2e8e4f2cd66441183104bb868837b26
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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