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Dichloromethane → (2-{2-[(Carboxy-phenyl-methyl)-carbamoyl]phenyldisulfanyl}-benzoylamino)-phenyl-acetic acid

HRID 3708
Notes
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Reaction equation

HRID 3708 reaction equation
C([O:5][C:6](=[O:48])[CH:7]([NH:14][C:15](=[O:47])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30](=[O:46])[NH:31][CH:32]([C:39]([O:41]C(C)(C)C)=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>CCOCC.CCCCCC>[C:6]([CH:7]([NH:14][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([NH:31][CH:32]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]([OH:41])=[O:40])=[O:46])=[O:47])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([OH:48])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 76120819(2-{2-[(tert-Butoxycarbonyl-phenyl-methyl)carbamoyl]-phenyldisulfanyl}-benzoylamino)phenyl-acetic acid tert-butyl ester

Product 1

HCID 465365(2-{2-[(Carboxy-phenyl-methyl)-carbamoyl]phenyldisulfanyl}-benzoylamino)-phenyl-acetic acidYield 42.5%

Reagents, catalysts & solvents 1

HCID 21584099
Diethylether hexane
Solvent

Procedure

This compound was prepared according to the procedure described in Example 50 using [R-(R*,R*)] (2-{2-[(tert-butoxycarbonyl-phenyl-methyl)-carbamoyl]-phenyldisulfanyl}-benzoylamino)-phenyl-acetic acid tert-butyl ester (0.2 g, 0.3 mmol) from Example 38, 10 mL dichloromethane, and 10 mL trifluoroacetic acid. The crude product was stirred with ether/hexane and filtered to afford 73.0 mg of the title compound, mp 231°-232° C.

Workup

  1. customThis compound was prepared
  2. filtrationfiltered

Sources & evidence

ORD record
ord-90c1ac43b2814299a03384dc402e2956
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05734081

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes