Diisopropylethylamine → N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-S-[[3-(methoxycarbonyl)phenyl]methyl]-L-cysteinamide

HRID 276729Notes

Reaction equation

HRID 276729 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][C@@H:6]([C:23]([NH:25][C:26](=[O:31])[C@H:27]([CH2:29][SH:30])[NH2:28])=[O:24])[NH:7][C:8](=[O:22])[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[CH2:36][C:37]1[CH:38]=[C:39]([CH:44]=[CH:45][CH:46]=1)[C:40]([O:42][CH3:43])=[O:41].C(N(C(C)C)CC)(C)C>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][C@@H:6]([C:23]([NH:25][C:26](=[O:31])[C@H:27]([CH2:29][S:30][CH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:39]([C:40]([O:42][CH3:43])=[O:41])[CH:38]=1)[NH2:28])=[O:24])[NH:7][C:8](=[O:22])[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 86591130N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-L-cysteinamide

Product 1

HCID 69265745N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-S-[[3-(methoxycarbonyl)phenyl]methyl]-L-cysteinamide

Procedure

A solution of N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-L-cysteinamide (0.72 g, 1.51 mmol), methyl 3-(bromomethyl)-benzoate (0.35 g, 1.51 mmol), and diisopropylethylamine (0.27 mL, 1.53 mmol) is stirred at room temperature overnight. Solvent is evaporated, and the residue is treated with 1 N HCl (50 mL), and filtered to collect a white solid, which is washed with water and Et2O (100 mL each). Drying in vacuo yields N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-S-[[3-(methoxycarbonyl)phenyl]methyl]-L-cysteinamide, as a white solid.

Workup

  1. customSolvent is evaporated
  2. additionthe residue is treated with 1 N HCl (50 mL)
  3. filtrationfiltered
  4. customto collect a white solid, which
  5. washis washed with water and Et2O (100 mL each)
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-02a54bc989d24a8b855d3bb335ac95a7
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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