Benzoic Acid → HCID 18513148, compound

HRID 1370755Notes

Reaction equation

HRID 1370755 reaction equation
C1C=[CH:5][C:4]([C:7](O)=O)=[CH:3]C=1.[C:10]1([S:16]([NH2:19])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:20]1([CH2:26][CH2:27][CH:28]=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([N+:34]#[C-:35])(C)(C)C.C1C[O:39]CC1>>[C:4]([C:28]([NH:19][S:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:18])=[O:17])([CH2:27][CH2:26][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:35]([NH2:34])=[O:39])([CH3:3])([CH3:5])[CH3:7]

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 7370BenzenesulfonamideHCID 7707BenzenepropanalHCID 8028TetrahydrofuranHCID 23577Tert-Butyl isocyanide

Product 1

HCID 18513148HCID 18513148, compound

Procedure

The preparation of Example 8 is illustrated in Scheme 11, in an 8 mL vial carboxypolystyrene resin (11-1) (100 mg) was swelled in 2 mL of THF. Then 2 mL of benzenesulfonamide solution (10 equiv., 1.0 M in THF), 2 mL of 3-phenylpropanal solution (10 equiv., 1.0 M in MeOH), and 2 mL of t-butyl isocyanide solution (10 equiv., 1.0 M in MeOH) were added. The suspension was mixed on an ACT Labmate at 60° C. for 24 h. Then the excess of reagent solution was removed by filtration and the resin (11-2) was washed and dried. The desired product was cleaved by treatment with a mixture of 48% aqueous methylamine and THF (2 mL, 1:1) for 12 h at room temperature. 1HNMR (CD3OD): δ 7.53-7.87 (m, 5H), 7.08-7.24 (m, 5H), 3.74 (t, 1H), 2.64(m, 1H), 2.48(m, 1H), 1.86 (m, 1H), 1.75 (m, 1H), 1.14 (s, 9H).

Workup

  1. customThe preparation of Example 8
  2. additionThe suspension was mixed on an ACT Labmate at 60° C. for 24 h
  3. customThen the excess of reagent solution was removed by filtration
  4. washthe resin (11-2) was washed
  5. customdried
  6. additionThe desired product was cleaved by treatment with a mixture of 48% aqueous methylamine and THF (2 mL, 1:1) for 12 h at room temperature

Sources & evidence

ORD record
ord-74f05ad29b404587a92b276df78ae94e
Source dataset
uspto-grants-2003_06
Patent number
US06583318B2

Reaction notes

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