Tetrahydrofuran → Methyl bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976038Notes

Reaction equation

HRID 976038 reaction equation
[CH3:1][NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:18]1([CH2:28][CH:29]([CH2:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)[C:30](Cl)=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.CCN(CC)CC.C1C[O:54]CC1>>[CH3:30][C:29]([CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)([CH2:28][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:1]([NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:54]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 14861533Bis-(1-naphthylmethyl)acetyl chlorideHCID 86750506methyl alpha-methyl-D-tryptophan

Product 1

HCID 86750505Methyl bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)Yield 88.9%

Procedure

A solution of 2.0 g (8.6 mmol) of methyl α-methyl-D-tryptophan in 30 mL THF was treated with 3.09 g (8.6 mmol) of bis-(1-naphthylmethyl)acetyl chloride (J. Med. Chem., 35:1032 (1992)) followed by 1.2 mL (8.6 mmol) of Et3N. After stirring at room temperature for 2 days, the solvent was removed under reduced pressure and the residue taken up in EtOAc and washed with 1HCl, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave 4.77 g of the crude product. Recrystallization from CH3CN/H2O gave 4.24 g (88.9% yield) of the product as a cream solid, mp 193°-195° C. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customthe solvent was removed under reduced pressure
  2. washwashed with 1HCl, H2O, saturated NaHCO3, and saturated NaCl
  3. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  4. customgave 4.77 g of the crude product
  5. customRecrystallization from CH3CN/H2O

Sources & evidence

ORD record
ord-7ed07fbcda7a47d681ad90327e7f0d90
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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