Lithium Hydroxide → HCID 178440046, compound

HRID 2374219Notes

Reaction equation

[C:1]1([O:7][P:8]([CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]2[N:25](CC3C=CN=CC=3)[C:26]([S:32][C:33]3[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=3)=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[O:21])(=[O:16])[O:9]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].[CH3:50][C:51]#[N:52]>>[C:1]1([O:7][P:8]([CH2:17][CH2:18][NH:19][C:20]([O:22][CH:23]([C:24]2[NH:25][C:26]([S:32][C:33]3[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=3)=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)[CH2:3][C:2]2[CH:1]=[CH:6][N:52]=[CH:51][CH:50]=2)=[O:21])(=[O:16])[OH:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 6342Acetonitrile

HCID 10101323HCID 10101323, compound

Product 1

HCID 178440046HCID 178440046, compoundYield 100%

Conditions

Temperature: 0 °C

Procedure

To a solution of phosphonate 31 (11 mg, 0.015 mmol) in CH3CN (0.5 mL) was added 1N LiOH (46 μL, 0.046 mmol) at 0° C. See Scheme 21 (FIG. 23). After the reaction mixture was stirred for 2 h at 0° C., Dowex 50WX8-200 (26 mg) was added and stirring was continued for an additional 30 min. The reaction mixture was filtered, rinsed with CH3CN, and concentrated under reduced pressure to give {2-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-ethyl }-phosphonic acid monophenyl ester 32 (10 mg, 100%) as a colorless oil. 1H NMR (300 MHz, CD3OD) δ 8.52 (d, 2H), 7.28 (m, 6H), 6.79 (m, 4H), 5.60 (s, 2H), 5.29 (s, 2H), 3.29 (m, 3H), 1.83 (m, 2H), 1.31 (d, 6H). 31P NMR (300 MHz, CD3OD) δ 20.2.

Workup

stirringstirring
waitwas continued for an additional 30 min
filtrationThe reaction mixture was filtered
washrinsed with CH3CN
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b82dc1ac1c5a4fef9e8560a10c8c151d
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462608B2

Reaction notes

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