Toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-isopropyl-phenyl) ester → Toluene-4-thiosulfonic acid S-(4,5-diamino-2-isopropyl-phenyl)ester

HRID 1859565Notes

Reaction equation

HRID 1859565 reaction equation
C(OC([NH:8][C:9]1[C:14]([NH:15]C(OC(C)(C)C)=O)=[CH:13][C:12]([S:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[C:11]([CH:34]([CH3:36])[CH3:35])[CH:10]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:8][C:9]1[C:14]([NH2:15])=[CH:13][C:12]([S:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[C:11]([CH:34]([CH3:36])[CH3:35])[CH:10]=1

Participants

3

Reactant 1

HCID 69753768Toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-isopropyl-phenyl) ester

Product 1

HCID 69734761Toluene-4-thiosulfonic acid S-(4,5-diamino-2-isopropyl-phenyl)ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-isopropyl-phenyl)ester (prepared in Example UU-1; 8.88 g, 16.6 mmol) was dissolved in CH2Cl2 (25 mL), and HCl gas was bubbled through the solution for 15 minutes. The reaction mixture was stirred at room temperature for 90 minutes. The solvents were evaporated, and the residue was dissolved in MeOH (10 mL) and treated with pH 7.5 buffer. The precipitate that formed was filtered and dried. MS(APCI): 337 (M+H).

Workup

  1. customHCl gas was bubbled through the solution for 15 minutes
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in MeOH (10 mL)
  4. additiontreated with pH 7.5 buffer
  5. customThe precipitate that formed
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-b566c186dab641468afa6d3823c932d2
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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