Trimethyl orthoformate → HCID 67103487, compound

HRID 2080885Notes

Reaction equation

HRID 2080885 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10].C(OC)(OC)OC.[C:21]([O:25][C:26](=[O:37])[NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=1)([CH3:24])([CH3:23])[CH3:22].[BH4-].[Na+]>CO>[C:21]([O:25][C:26](=[O:37])[NH:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])=[CH:33][CH:34]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydrideHCID 23155392HCID 23155392, compound

Product 1

HCID 67103487HCID 67103487, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (81.0 mg) obtained in Example 90-3 was dissolved in anhydrous methanol (2.0 ml) and added with trimethyl orthoformate (94.1 μl) and the compound (101 mg) obtained in Example 23-3 and the whole was stirred overnight at room temperature under a nitrogen atmosphere. Subsequently, sodium borohydride (32.6 mg) was added thereto in an ice bath and the whole was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with distilled water and the whole was stirred for a while. The resultant was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (158 mg) as a colorless oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. additionadded with distilled water
  5. stirringthe whole was stirred for a while
  6. extractionThe resultant was subjected to extraction with chloroform
  7. washwashed with a saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7cb21eca34714b498ccd5ba959645c4b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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