Ammonia → HCID 59253308, compound

HRID 2092499Notes

Reaction equation

HRID 2092499 reaction equation
[F:1][C:2]([F:23])([F:22])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:21])[C:17](=O)[O:16]C(C)(C)[O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[NH3:24]>>[F:1][C:2]([F:23])([F:22])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:14])([CH3:21])[C:17]([NH2:24])=[O:16])=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86640272HCID 86640272, compound

Product 1

HCID 59253308HCID 59253308, compoundYield 70%

Procedure

A solution of 4-(2,2,4-trimethyl-5-oxo-1,3-dioxolan-4-yl)phenyl trifluoromethanesulfonate (15.5 g, 0.044 mol) in ammonia solution (30 mL, 7N in methanol) was left under stirring overnight at room temperature. After solvent evaporation under vacuum a crude was obtained that, after purification by flash chromatography (CH2Cl2/MeOH 98:2) afforded pure 2-[4-(trifluoromethanesulfonyloxy)phenyl]-2-hydroxy propanamide (9.7 g, 0.031 mol) as a white solid. Yield 70%. mp 105-107° C. 1H-NMR (CDCl3) δ 7.80 (d, 2H, J=7 Hz), 7.35 (d, 2H, J=7 Hz), 6.50 (bs, 1H, CONH), 5.42 (bs, 1H, CONH), 3.05 (bs, 1H, OH), 1.94 (s, 3H).

Workup

  1. customAfter solvent evaporation under vacuum a crude
  2. customwas obtained that,
  3. customafter purification by flash chromatography (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-69cfa8eaa08540648b53f832ecf53398
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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