Diazomethane → HCID 59814862, compound

HRID 2116641Notes

Reaction equation

HRID 2116641 reaction equation
[F:1][C:2]([F:34])([F:33])[C@:3]([C:9]1[S:13][C:12]([S:14][C:15]2[CH:24]=[C:23]3[C:18]([C:19]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:20][C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)=[N:11][CH:10]=1)([OH:8])[CH2:4][C:5]([OH:7])=[O:6].[N+](=[CH2:37])=[N-]>C1COCC1>[F:34][C:2]([F:1])([F:33])[C@:3]([C:9]1[S:13][C:12]([S:14][C:15]2[CH:24]=[C:23]3[C:18]([C:19]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)=[CH:20][C:21](=[O:25])[O:22]3)=[CH:17][CH:16]=2)=[N:11][CH:10]=1)([OH:8])[CH2:4][C:5]([O:7][CH3:37])=[O:6]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 59814859HCID 59814859, compound

Product 1

HCID 59814862HCID 59814862, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R)-4,4,4-trifluoro-3-(2-{[4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl]thio}-1,3-thiazol-5-yl)-3-hydroxybutanoic acid (see example 12, step 4b) (0.140 g, 0.27 mmol) in THF was added an ethereal solution of diazomethane until the evolution of gas was finished. The solvent was removed to yield 0.120 g of the crude title compound. 1H NMR (400 MHz, acetone-d6): δ 7.96 (s, 1H), 7.77 (m, 2H), 7.58 (m, 2H), 7.48 (d, 1H), 7.39 (t, 2H), 6.53, (s, 1H), 6.42 (s, 1H), 3.63 (s, 3H), 3.40 (d, 1H), 3.25 (d, 1H).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-48804a00957f4b22a652e97023f1ca1b
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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