2-Naphthol → HCID 67031597, compound

HRID 1716537Notes

Reaction equation

HRID 1716537 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[C:12]([O:16][C:17]([N:19]1[C@@H:23]([CH3:24])[CH2:22]OS1(=O)=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH4+].[Cl-]>CN(C=O)C>[C:12]([O:16][C:17](=[O:18])[NH:19][C@@H:23]([CH3:22])[CH2:24][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 25517Ammonium ChlorideHCID 109882941,2,3-Oxathiazolidine-3-carboxylic acid, 4-methyl-, 1,1-dimethylethyl ester, 2,2-dioxide, (4S)-

Product 1

HCID 67031597HCID 67031597, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

β-Naphthol (721 mg) was dissolved in DMF (25 mL) and cooled to 0° C. Potassium-tert-butylate (1M in THF, 6.0 mL) was added drop by drop over a period of 15 minutes and the mixture was stirred for 30 min. (S)-4-Methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (IV, 1.42 g) was added in one portion and stirring was continued for 3 hours. The reaction mixture was poured into 1M NH4Cl and extracted with ether. The organic phase washed with 1M NH4Cl and brine, dried over Na2SO4 and evaporated to yield a yellow solid. The crude product was purified by flash chromatography (ethyl acetate/hexanes 1:9) to give the desired product as a colorless solid (1.5 g).

Workup

  1. additionwas added in one portion
  2. extractionextracted with ether
  3. washThe organic phase washed with 1M NH4Cl and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto yield a yellow solid
  7. customThe crude product was purified by flash chromatography (ethyl acetate/hexanes 1:9)

Sources & evidence

ORD record
ord-e8d93ad04d714e619da95e5e644fdff1
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

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