Dicyclohexylcarbodiimide → HCID 131714159, compound

HRID 2164485Notes

Reaction equation

HRID 2164485 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26](O)=[O:27])[CH3:25])=[O:22])[CH2:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:10])[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].O1CCOCC1.[OH:42][N:43]1[C:48](=[O:49])[CH2:47][CH2:46][C:44]1=[O:45].C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[NH2:1][C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26]([O:42][N:43]1[C:48](=[O:49])[CH2:47][CH2:46][C:44]1=[O:45])=[O:27])[CH3:25])=[O:22])[CH2:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:10])[CH2:3][O:4][C:5]([CH3:7])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 131714160HCID 131714160, compound

Product 1

HCID 131714159HCID 131714159, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Boc-Ser(tBu)-Asp(OtBu)-Ala-OH.CHA (1.205 g, 2.0 mmol) was extracted with a mixture of EtOAc: 0.5N H2SO4 (10 mL-10 mL). The organic layer was retained, washed with saturated NaCl, dried (MgSO4) and evaporated in vacuo. The resultant free acid in EtOAc:dioxane (5 mL-10 mL) was treated with HOSu (230 mg, 2.0 mmol, 1 eq) and cooled to 0°. To the cold stirring solution DCC (412 mg, 2.0 mm, 1 eq) was added portionwise and stirring proceeded at 0° for 1 hr and at 25° for 48 hr. The reaction mixture was filtered and the filtrate evaporated to dryness and crystallized from isopropanol-petroleum ether. Yield: 631 mg (52.5%); mp 129°-136°; [α]D25 -32.74° (c 1, MeOH); Rf 0.86 (CHCl3 :MeOH:AcOH; 85-10-5); Rf 0.79 (CHCl3 :MeOH:AcOH; 80-5-2). Anal. calc. for C27H44N4O11 (600.67): C, 53.99; H, 7.38; N, 9.33. Found C, 53.85; H, 7.50; N, 9.29.

Workup

  1. extractionCHA (1.205 g, 2.0 mmol) was extracted with a mixture of EtOAc
  2. washwashed with saturated NaCl
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. temperaturecooled to 0°
  6. filtrationThe reaction mixture was filtered
  7. customthe filtrate evaporated to dryness
  8. customcrystallized from isopropanol-petroleum ether

Sources & evidence

ORD record
ord-2d36742cff2f40b9b9cda8dfa7c2c613
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

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