Trimethyl orthoformate → HCID 69762977, compound

HRID 1006115Notes

Reaction equation

HRID 1006115 reaction equation
[C:1]([O:5][C:6](=[O:32])[C@H:7]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([NH2:31])[CH:25]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH:33](OC)(OC)OC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:32])[C@H:7]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]2[N:30]=[CH:33][NH:31][C:26]=2[CH:25]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 69762753HCID 69762753, compound

Product 1

HCID 69762977HCID 69762977, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2(R)-{[(3,4-diamino)benzyl]-(4-methoxybenzenesulfonyl)amino}-3-methylbutyric acid tert-butyl ester (90 mg, 0.194 mmol) and trimethyl orthoformate (0.022 mL, 1.05 equiv.) in dry toluene (10 mL) was added KSF montmorillonite clay (25 mg). The reaction mixture was heated at reflux for 6.5 h and then cooled to room temperature. After reaching room temperature, the mixture was condensed in vacuo and the residue was loaded onto a preparatory thin layer chromatography plate. Elution with methanol/methylene chloride (10%) provided 2(R)-[(benzimidazol-5-ylmethyl)-(4-methoxy-benzenesulfonyl)amino]-3-methylbutyric acid tert-butyl ester (79 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6.5 h
  3. customAfter reaching room temperature
  4. customcondensed in vacuo
  5. washElution with methanol/methylene chloride (10%)

Sources & evidence

ORD record
ord-81486cc5204b4dd795d155aa604355ed
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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