Potassium Carbonate → HCID 12069132, compound

HRID 1356203Notes

Reaction equation

HRID 1356203 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([CH2:10][C@@H:11]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6][C:5]=1[OH:30].C([O-])([O-])=O.[K+].[K+].[C:38]([O:41][CH2:42]Br)(=[O:40])[CH3:39]>CC(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([CH2:10][C@@H:11]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6][C:5]=1[O:30][CH2:39][C:38]([O:41][CH3:42])=[O:40]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68536Bromomethyl acetateHCID 12069131HCID 12069131, compound

Product 1

HCID 12069132HCID 12069132, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-((2S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-2-hydroxy-benzoic acid methyl ester of Step C (213 mg, 0.49 mmol) is stirred in acetone (2 mL) with powdered K2CO3 (207 mg, 1.5 mmol) and bromomethyl acetate (95uL, 1.5 mmol) at RT under N2 and then at 50° C. The reaction is diluted with EtOAc (100 mL) and washed with 1N HCl (30 mL) and saturated NaHCO3 (2×30 mL). The organics are dried (MgSO4), filtered, concentrated and purified by flash column chromatography to provide 5-((2S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-2-methoxycarbonylmethoxy-benzoic acid methyl ester.

Workup

  1. customat 50° C
  2. washwashed with 1N HCl (30 mL) and saturated NaHCO3 (2×30 mL)
  3. dry with materialThe organics are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-0ac5eb8d9d39403d9b0a2374414c1a46
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

Loading…