Urea → HCID 66758914, compound

HRID 556928Notes

Reaction equation

HRID 556928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([CH:32]=O)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:35][C:36]([NH2:38])=[O:37].C[Si](Cl)(C)C.[BH4-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([CH2:32][NH:35][C:36]([NH2:38])=[O:37])[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1176UreaHCID 6397ChlorotrimethylsilaneHCID 4311764Sodium borohydrideHCID 86585735HCID 86585735, compound

Product 1

HCID 66758914HCID 66758914, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the product of example 314 (800 mg) in acetic acid (20 ml) were added urea (2 g) and trimethylsilyl chloride (0.24 ml) at room temperature, and the mixture stirred for 2 hours. Sodium borohydride was added to the reaction mixture at room temperature, and the mixture was stirred for 1 hour. The solvent was distilled off under reduced pressure, and, chloroform, 2-propanol and water were added. The organic layer was extracted, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with chloroform-methanol-ammonium hydroxide (100:10:1) to give the titled compound (250 mg).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure, and, chloroform, 2-propanol and water
  3. additionwere added
  4. extractionThe organic layer was extracted
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with chloroform-methanol-ammonium hydroxide (100:10:1)

Sources & evidence

ORD record
ord-608829c2430641298fa64fa43979b4f7
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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