N-(t-butoxycarbonyl-sulfamoyl)-N-[2-(methoxycarbonylmethyl)-phenyl]-glycine t-butyl ester → N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl]glycine

HRID 1592021Notes

Reaction equation

HRID 1592021 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][N:8]([S:20](=[O:30])(=[O:29])[NH:21]C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[S:20]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:7][C:6]([OH:31])=[O:5])(=[O:30])(=[O:29])[NH2:21]

Participants

4

Reactant 1

HCID 67138370N-(t-butoxycarbonyl-sulfamoyl)-N-[2-(methoxycarbonylmethyl)-phenyl]-glycine t-butyl ester

Product 1

HCID 67138346N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl]glycine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The title D compound, N-(t-butoxycarbonyl-sulfamoyl)-N-[2-(methoxycarbonyl-methyl)-phenyl]-glycine t-butyl ester (1.87 g, 4.07 mmol) is dissolved in a mixture of TFA (35 mL) and CH2Cl2 (35 mL) and stirred for 30 min. The reaction is concentrated in vacuo, then triturated with diethyl ether to yield N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl]glycine as a clear glass.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-27fa49cb78b84887b32bc4d9df79f8c9
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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