Dicyclohexylcarbodiimide → HCID 13501924, compound

HRID 2164481Notes

Reaction equation

HRID 2164481 reaction equation
[NH:1]([C:29]([CH3:31])=[O:30])[C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26]([OH:28])=[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].O[N:33]1[C:38](=[O:39])[CH2:37][CH2:36][C:34]1=[O:35].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:29]([CH3:31])=[O:30])[C@H:2]([C:9]([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:26]([O:28][N:33]1[C:38](=[O:39])[CH2:37][CH2:36][C:34]1=[O:35])=[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]([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 13501988HCID 13501988, compound

Product 1

HCID 13501924HCID 13501924, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Ac-Ser(tBu)-Asp(OtBu)-Ala-OH (24.7 g, 55.4 mmol) in dry THF (526 mL) was treated with HOSu (9.55 g, 83.1 mmol, 1.5 eq.) and cooled to 0°. To the cold stirring (mechanical) solution DCC (17.14 g, 83.1 mmol, 1.5 eq.) was added portionwise and stirring proceeded at 0° for 30 min at 25° for 5 h. The reaction mixture was filtered and the filtrate evaporated to dryness and crystallized from isopropanol (250 mL). Yield: 23.2 g (77.2%); mp 155°-157°; [α]D25 -41.48° (c 1, MeOH); Rf 0.54 (CHCl3 :MeOH:AcOH; 80-5-1). Anal. calc. for C24H38N4O10 (542.58): C, 53.13; H, 7.06; N, 10.33. Found: C, 53.21; H, 6.85; N, 10.29.

Workup

  1. temperaturecooled to 0°
  2. additionwas added portionwise
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. customcrystallized from isopropanol (250 mL)

Sources & evidence

ORD record
ord-c676a3e0687d407e8b04ac1200ab6d04
Source dataset
uspto-grants-1985_03
Patent number
US04504415

Reaction notes

Loading…