Tetrahydrofuran → HCID 12919642, compound

HRID 1156942Notes

Reaction equation

HRID 1156942 reaction equation
[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]

Participants

5

Reactant 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

Product 1

HCID 12919642HCID 12919642, compound

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6fc956d9371342cf8ae744c85243c44c
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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