Methanol → HCID 66917685, compound

HRID 1817997Notes

Reaction equation

HRID 1817997 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][NH:6][C:7]1[C:12]2[N:13]([CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)[C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=[CH:9][CH:8]=1)C.CO.[OH-].[Na+]>C1COCC1>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][N:13]1[C:12]2[C:7]([NH:6][CH2:5][C:4]([OH:29])=[O:3])=[CH:8][CH:9]=[CH:10][C:11]=2[O:16][CH2:15][C:14]1=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66917943HCID 66917943, compound

Product 1

HCID 66917685HCID 66917685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4-naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamino)-acetic acid ethyl ester, I-63 (105 mg), methanol (3.0 mL), THF (2.0 mL) and 2.0 M NaOH (0.5 mL) was stirred at room temperature for 18 h. Methanol was evaporated and the residue was taken water (3.0 mL) and acidified to pH 1 with 2.0 M HCl resulting in the precipitation of a white solid. Solid was extracted with chloroform (10 mL×2), and the combined extracts were dried (brine, anhydrous sodium sulfate), concentrated and dried on high vacuum to afford (4-naphthalen-2-ylmethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamino)-acetic acid, I-64 (102 mg).

Workup

  1. customMethanol was evaporated
  2. customacidified to pH 1 with 2.0 M HCl resulting in the precipitation of a white solid
  3. extractionSolid was extracted with chloroform (10 mL×2)
  4. dry with materialthe combined extracts were dried (brine, anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customdried on high vacuum

Sources & evidence

ORD record
ord-578d305aa2f64b24a823926597d53891
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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