Pyridine → 3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester

HRID 1814377Notes

Reaction equation

HRID 1814377 reaction equation
C(Cl)Cl.[CH3:4][O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1.[C:26]([O:30][C:31](=[O:38])[CH2:32][C@H:33]([NH2:37])[C:34]([NH2:36])=[O:35])([CH3:29])([CH3:28])[CH3:27].N1C=CC=CC=1>C(OCC)(=O)C>[CH3:4][O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([S:13](=[O:15])(=[O:14])[NH:37][C@H:33]([C:34](=[O:35])[NH2:36])[CH2:32][C:31]([O:30][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:38])=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7019655L-Aspartic alpha-amide beta-t-butyl esterHCID 865882243-Benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester

Product 1

HCID 697302973-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature CH2Cl2 solution (400 mL) of 3-benzyloxy-4-chlorosulfonyl-benzoic acid methyl ester (11.43 g, 33.50 mmol) was added (S)-3-amino-succinamic acid tert-butyl ester (6.32 g, 33.50 mmol) and pyridine (10.80 mL). The reaction mixture was allowed to stir for 12 h at room temperature. The reaction was then diluted with ethyl acetate and washed with 5% citric acid and saturated NaHCO3. The organic phase was dried (MgSO4), and then the solvent was removed under vacuum. The resulting crude product was purified using silica gel flash chromatography (3% MeOH in CH2Cl2). 3-Benzyloxy-4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-benzoic acid methyl ester was obtained in 45% yield (7.40 g) as an off white foam. MS m/z 491.2 (M−1).

Workup

  1. washwashed with 5% citric acid and saturated NaHCO3
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent was removed under vacuum
  4. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-725dfbf350364d38a96f5a25d43022d9
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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