Sodium Hydroxide → HCID 19039984, compound

HRID 1684615Notes

Reaction equation

HRID 1684615 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][C:15]3[CH:16]=[C:17]([NH:21][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[C:10]2=[O:13])=[CH:5][CH:4]=1.[OH-].[Na+]>Br.C(O)(=O)C.O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][C:15]3[CH:16]=[C:17]([NH:21][S:22]([C:25]([F:28])([F:26])[F:27])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 19039957HCID 19039957, compound

Product 1

HCID 19039984HCID 19039984, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A mixture of 439 mg (1.06 mmol) of the product of Example 30 in 8 mL 48% HBr and 8 mL acetic acid was heated to reflux for 75 minutes under N2. The reaction mixture was cooled to room temperature, diluted with 300 mL H2O, pH adjusted to 3-4 using 2N NaOH, and extracted with twice with 150 mL ethyl acetate. The ethyl acetate extracts were combined and washed once with brine and then dried over Na2SO4. Filtration, concentration and drying yielded 0.42 g of tan solid, which was purified by silica gel chromatography (4% methanol-CH2Cl2) to yield 357 mg of pure product, an off-white powder. (84% yield) m.p.: 191°-194° C.; MS (LSIMS): 400 M+H, Base; 1H NMR (AC 300, dimethylsulfoxide-d6): δ9.58 (br s, 1H, phenol OH); IR (cm31 1): 3330, 3280, 1670. Analysis calculated: C 54.13, H 4.04, N 3.51%; C 53.99, H 3.95, N 3.49%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 75 minutes under N2
  3. extractionextracted with twice with 150 mL ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration, concentration
  7. customdrying

Sources & evidence

ORD record
ord-6c48b05e547c4d8e8528cfcdcb9cb423
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

Loading…