Acetic Acid → HCID 69332915, compound

HRID 354460Notes

Reaction equation

HRID 354460 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[CH2:28][NH:29][C@@H:30]2[CH2:35][CH2:34][C@H:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][CH2:31]2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].C=O.[CH3:42]C(O)=O.[BH3-]C#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[CH2:28][N:29]([CH:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][CH2:31]2)[CH3:42])=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178491572HCID 178491572, compound

Product 1

HCID 69332915HCID 69332915, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl cis-4-[[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylate (300 mg, 0.55 mmol), HCHO (300 ml), and AcOH (66 mg, 1.1 mmol) in MeOH (10.0 ml) was added NaBH3CN (70 mg, 1.1 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. After concentrated in vacuo, water was added and extracted with CH2Cl2. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo. The residue was purified by TLC with MeOH—CH2Cl2 (3:97, v/v) as eluent to give methyl 4-[N-[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethyl]-N-methylamino]cyclohexanecarboxylate (160 mg, 52%) as an amorphous solid. 1H-NMR (CDCl3) δ1.30-2.20 (m, 12H), 2.27-2.37 (m, 6H), 2.50-2.60 (m, 1H), 3.30-3.80 (m, 5H), 3.55 (s, 2H, 3.66-3.73 (m, 6H), 4.10-4.20 (m, 1H), 6.60-7.55 (m, 7H), 8.03 (m, 1H), 8.15 (m, 1H).

Workup

  1. concentrationAfter concentrated in vacuo, water
  2. additionwas added
  3. extractionextracted with CH2Cl2
  4. washThe extract was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by TLC with MeOH—CH2Cl2 (3:97

Sources & evidence

ORD record
ord-1f0df210617e40968bff65e06b6256e3
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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