1,3-Propanedithiol → 4(Aminomethyl)-2-phenylbenzoyl methionine methyl ester

HRID 383092Notes

Reaction equation

HRID 383092 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]=[N+]=[N-])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C(S)CCS>CO>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 20622822[4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 206228204(Aminomethyl)-2-phenylbenzoyl methionine methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the resultant compound from Example 18A in methanol is added triethylamine (3.0 equivalent) and propane 1,3-dithiol (3.0 equivalents). After the reaction is judged complete by TLC analysis, the mixture is filtered and evaporated. Chromatography of the residue on silica gel provides the title product.

Workup

  1. filtrationthe mixture is filtered
  2. customevaporated

Sources & evidence

ORD record
ord-8b5cc950e3fa41f3a6d54ec4ba6939b5
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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