1,4-Dioxane → 1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate

HRID 2078101Notes

Reaction equation

HRID 2078101 reaction equation
CCN([CH:7]([CH3:9])[CH3:8])C(C)C.Cl.[NH2:11][C@H:12]([C:17]([OH:19])=[O:18])C(C)(C)C.[OH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[C:31]([F:34])([F:33])[F:32])[C:24]([CH3:36])([CH3:35])[C:23](=[O:37])[C:22]=1[C:38](OCC)=[O:39].O1CCOC[CH2:44]1>>[OH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[C:31]([F:34])([F:32])[F:33])[C:24]([CH3:36])([CH3:35])[C:23](=[O:37])[C:22]=1[C:38]([NH:11][CH2:12][C:17]([O:19][C:7]([CH3:8])([CH3:9])[CH3:44])=[O:18])=[O:39]

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 123146853-Methyl-L-valine hydrochlorideHCID 67099721Ethyl 4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalene-3-carboxylate

Product 1

HCID 670997161,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate

Procedure

DIPEA (40 μL, 0.23 mmol), tert-butylglycine hydrochloride (38 mg), and ethyl 4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalene-3-carboxylate (50 mg, 0.15 mmol) were heated in dioxane (2 mL) for 5 hours, cooled to room temperature, and then concentrated under vacuum. The residue was purified by column chromatography to give the product as a yellow oil (30 mg). MS (m/z)=358.4 [M-tBu]+

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2f9a471c9da047c6ad7e3a77ce46432f
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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