1-Hydroxybenzotriazole → HCID 131719302, compound

HRID 1440163Notes

Reaction equation

HRID 1440163 reaction equation
[NH2:1][C@@H:2]([C:14]([NH:16][C@@H:17]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1.[NH:32]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:33]([C:38](O)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36].O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>ClCCl.C(OCC)(=O)C.O>[NH:32]([C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])[C@H:33]([C:38]([NH:1][C@@H:2]([C:14]([NH:16][C@@H:17]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:15])[CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][CH:5]=1)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12373896N-Boc-L-Leucine HydrateHCID 131719300HCID 131719300, compound

Product 1

HCID 131719302HCID 131719302, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of H-DNal-DNle-OBzl (180 mg, prepared in (2)) in dichloromethane (5 ml) were added Boc-Leu-OH.H2O (180 mg), HOBT.H2O (70 mg) and EDCI.HCl (99 mg) successively under ice cooling. After being stirred at room temperature for 14 h, the mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3, 10% aq. citric acid, water and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by dry column flash chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=1/2 for elution to give Boc-Leu-DNal-DNle-OBzl (239 mg). A solution of the tripeptide derivative (87 mg) in 95% ethanol (10 ml) was hydrogenated over 10% Pd/C (21 mg) at an atmospheric pressure of hydrogen for 1 h. After removal of the catalyst by filtration, the filtrate was concentrated in vacuo to give Compound 16 (74 mg).

Workup

  1. washwashed with sat. aq. NaHCO3, 10% aq. citric acid, water and brine successively
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified
  5. dry with materialby dry column flash chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=1/2
  6. washfor elution

Sources & evidence

ORD record
ord-7b76a2374fba4e80894106682fed7054
Source dataset
uspto-grants-1996_03
Patent number
US05496928

Reaction notes

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