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Tetrahydrofuran → Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

HRID 1156942
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HRID 1156942 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][S:5][CH3:6].C1C2[CH:22]3[C:27](=[O:28])N(O)C(=O)C3C1C=C2.C1CC[CH:33]([N:36]=C=NC2CCCCC2)[CH2:32]C1.C1C[O:48]CC1>>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([NH:36][CH2:33][C:32]([O:28][CH2:27][CH3:22])=[O:48])=[O:9])[CH2:3][CH2:4][S:5][CH3:6]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 111051N-(tert-Butyloxycarbonyl)-D-methionine

생성물 1

HCID 12919642Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

반응 조건

온도
0 °C

실험 절차

In 100 ml of THF are dissolved 10.0 g of BOC-(D)-Met-OH and 7.9 g of HONB, and after cooling to 0° C., 9.0 g of DCC is added. The mixture is stirred at 0° C. for 6 hours. The insolubles are filtered off, 5.9 g of H-Gly-OEt.hydrochloride and 5.6 ml of TEA are added to the filtrate and the mixture is stirred at room temperature overnight. The THF is distilled off and the residue is extracted with 100 ml of AcOEt, washed with water and dried over anhydrous sodium sulfate. The AcOEt is distilled off and the residue is crystallized from petroleum benzine and further recrystallized from AcOEt-petroleum benzine. Yield 9.8 g; m.p. 55°-56° C.; Rf1 =0.70; [α]D21 +12.5° (c=0.67, DMF).

후처리

  1. filtrationThe insolubles are filtered off
  2. addition5.9 g of H-Gly-OEt.hydrochloride and 5.6 ml of TEA are added to the filtrate
  3. stirringthe mixture is stirred at room temperature overnight
  4. distillationThe THF is distilled off
  5. extractionthe residue is extracted with 100 ml of AcOEt
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe AcOEt is distilled off
  9. customthe residue is crystallized from petroleum benzine
  10. customfurther recrystallized from AcOEt-petroleum benzine

출처 및 근거

ORD 기록
ord-6fc956d9371342cf8ae744c85243c44c
출처 데이터셋
uspto-grants-1982_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04337247

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