Glycine → HCID 2060367、化合物

HRID 1249297ノート

反応式

HRID 1249297 の反応式
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].[NH2:17][CH2:18][C:19]([OH:21])=[O:20].[CH2:22](N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C@@H:2]([C:4]([NH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:6])[CH3:3]

参加物

7

反応物 5

HCID 750GlycineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 757711-Hydroxybenzotriazole

生成物 1

HCID 2060367HCID 2060367、化合物収率 84.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of Z-D-Ala (2.23 g, 10 mmol) and Gly.OMe.HCl (1.26 g, 10 mmol) in THF (50 ml) was chilled to 0° C. and triethylamine (1.01 g, 10 mmol), HOBt (1.35 g, 10 mmol) and DCC (2.06 f, 10 mmol) was added successively at 0° C. with stirring. After stirring for 4 hrs at 0° C., the reaction mixture was stirred at room temperature overnight and the precipitated crystals were filtered and the filtrate was evaporated in vacuo. The residue was extracted with ethyl acetate and the extract was washed with 5% citric acid, 5% NaHCO3 and water successively, and dried over anhyd. Na2SO4. The solvent was removed in vacuo and the resulting solid was recrystallized from ethyl acetate-hexane to give Z-D-Ala-Gly-OMe (26) (2.48 g, 84.4%) as colorless needles, mp 96°-97° C.; [α]D22 23.3° (c=1.0, MeOH): NMR (CDCl3)δ:1.39 (3H, d, J=8 Hz, CH3), 3.76 (3H, s CH3O), 4.03 (2H, d, J=6 Hz, CH2NH), 4.15-4.50 (1H, m, --CH--NH), 5.15, (2H, s, CH2O), 5.58 (1H, d, J=7 Hz, NH), 6.70-6.95 (1H, br, NH), 7.42 (5H, s, Ar--H). Rf (I)=0.62, Rf (VI)=0.38.

後処理

  1. stirringAfter stirring for 4 hrs at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. filtrationthe precipitated crystals were filtered
  4. customthe filtrate was evaporated in vacuo
  5. extractionThe residue was extracted with ethyl acetate
  6. washthe extract was washed with 5% citric acid, 5% NaHCO3 and water successively
  7. customdried over anhyd
  8. customThe solvent was removed in vacuo
  9. customthe resulting solid was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-b72e596b62b244219d053187931f1834
出典データセット
uspto-grants-1986_12
特許番号
US04629784

反応ノート

読み込み中…