Citric Acid → HCID 18433611, compound

HRID 2306269Notes

Reaction equation

HRID 2306269 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20]([Si:23](Cl)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21].N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:20]([CH3:22])[CH3:21])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

Product 1

HCID 18433611HCID 18433611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-(tert-butoxycarbonylamino)-2-naphthol, as described in Example 9, Step A, (8.00 g, 30.9 mmol), triisopropylsilyl chloride (7.92 mL, 37.0 mmol), and imidazole (4.20 g, 61.7 mmol) in DMF (75 mL) was stirred at ambient temperature for 18 hours, then poured into 10% aqueous citric acid (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with H2O, then brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with CH2Cl2—50% hexane to yield the desired product.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washThe combined organic extracts were washed with H2O
  3. dry with materialbrine, then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica
  7. washeluting with CH2Cl2—50% hexane

Sources & evidence

ORD record
ord-9cc3010c2d4746ff860b8b68d41e5261
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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