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

HRID 2121128Notes

Reaction equation

HRID 2121128 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-78e2544329cb41778fdc94f3044a55af
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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