HCID 68525551, compound → HCID 68764170, compound

HRID 1170418Notes

Reaction equation

HRID 1170418 reaction equation
C(OC(=O)[NH:7][C@:8]([CH2:20][O:21][P:22]([O:29]C(C)(C)C)([O:24]C(C)(C)C)=[O:23])([CH3:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)(C)(C)C.[ClH:35].C(O[C:39](=N)[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:47][CH3:48])[CH:41]=1)C>CO>[ClH:35].[NH2:7][C@:8]([CH3:19])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]2[O:17][C:39]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:47][CH3:48])[CH:41]=3)=[N:18][C:13]=2[CH:12]=1)[CH2:20][O:21][P:22](=[O:23])([OH:24])[OH:29]

Participants

4

Reactant 2

HCID 68525551HCID 68525551, compoundHCID 68767644HCID 68767644, compound

Product 1

HCID 68764170HCID 68764170, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [(R)-3-(3-Amino-4-hydroxy-phenyl)-1-(di-tert-butoxy-phosphoryloxymethyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (157.5 mg, 0.313 mmol) and 3-ethoxy-benzimidic acid ethyl ester hydrochloride in dry methanol (2 mL) was stirred for 20 minutes at 120° C. in a closed vial (microwave reactor). After cooling to RT the precipitate was filtered off, washed 2× with MeOH, 3× with water and 3× with diethyl ether. After drying in vacuum, the precipitate was dissolved in a mixture of diethyl ether/HCl (4 mL, 2M) and methanol (1 mL). After evaporation of the solvents the title compound was obtained as colorless crystals. 1H-NMR (CD3OD): δ=7.76 (d; 1H), 7.71 (s; 1H), 7.61 (bs; 2H), 7.47 (m; 1H), 7.37 (m; 1H), 7.14 (d; 1H), 4.24-4.00 (m; 4H), 2.89 (m; 2H), 2.10 (m; 2H), 1.47 (s; 6H); MS (ESI+): 421.4 [M+H]+

Workup

  1. filtrationwas filtered off
  2. washwashed 2× with MeOH, 3× with water and 3× with diethyl ether
  3. customAfter drying in vacuum
  4. dissolutionthe precipitate was dissolved in a mixture of diethyl ether/HCl (4 mL, 2M) and methanol (1 mL)
  5. customAfter evaporation of the solvents the title compound
  6. customwas obtained as colorless crystals

Sources & evidence

ORD record
ord-b336a2f79c2f4b41a022b12b88f63122
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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