Dimethylformamide → HCID 53678371, compound

HRID 611614Notes

Reaction equation

[OH:1][C@H:2]([C:5]1[CH:6]=[CH:7][C:8](CC(N)=O)=[N:9][CH:10]=1)[CH2:3][OH:4].[CH2:15]([N:17](CC)CC)[CH3:16].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].CN(C=[O:39])C>C(OCC)(=O)C>[C:15]([NH:17][C:8]1[N:9]=[CH:10][C:5]([C@@H:2]([OH:1])[CH2:3][O:4][S:31]([C:28]2[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)(=[O:33])=[O:32])=[CH:6][CH:7]=1)(=[O:39])[CH3:16]

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of (R)-(5-(1,2-dihydroxy-ethyl)-pyridin-2-yl)-acetamide (0.294, 1.5 mmol) in anhydrous DMF (3 ml) was treated with triethylamine (0.63 g, 4.5 mmol) and cooled to -40° C. A solution of 4-nitrobenzenesulfonyl chloride (0.332 g, 1.5 mmol) in ethyl acetate (3 ml) was added dropwise. After 45 minutes at -45° C., the mixture was stirred for one hour at 20° C. The mixture was then diluted with ethyl acetate and washed sequentially with water, twice with pH 6.6 buffer (0.1 M phosphate), water and brine. The ethyl acetate layer was dried over sodium sulfate, filtered and evaporated. The residue was triturated with 1,2-dichloroethane to give 0.381 g (67%) of the title product as colorless crystals. mp 116-120° C. with decomposition. 1H NMR (dmso-d6): δ=8.36 (d, 2 H); 8.16 (d, 1 H); 8.04 (d, 2 H); 7.91 (d, 1 H); 7.62 (d of d, 1 H); 5.89 (d, 1 H); 4.81 (d of d, 1 H); 4.24 (d, 2 H); 2.06 (s, 3 H). MS (Cl): m/z=179 (M+H+O2NC6H4SO3H).

Workup

washwashed sequentially with water, twice with pH 6.6 buffer (0.1 M phosphate), water and brine
dry with materialThe ethyl acetate layer was dried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue was triturated with 1,2-dichloroethane

Sources & evidence

ORD record: ord-243f1c8c3b5648579f996c46e3f88cb2
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06001856

Reaction notes

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