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

HRID 976038노트

반응식

HRID 976038 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ed07fbcda7a47d681ad90327e7f0d90
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610177

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