Glycine → HCID 2060367, 화합물

HRID 1249297노트

반응식

HRID 1249297 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

HCID 2060367HCID 2060367, 화합물수율 84.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b72e596b62b244219d053187931f1834
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04629784

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