Butyryl chloride → HCID 70047688, compound

HRID 1291800Notes

Reaction equation

HRID 1291800 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:7][C@H:8]([C@@H:30]([NH:38][C:39](=[O:58])[C@H:40]([CH2:54][C:55](=[O:57])[NH2:56])[NH:41][C:42]([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[N:45]=1)=[O:43])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:11][C:12](=[O:22])[C@H:13]([CH:19]([CH3:21])[CH3:20])[NH:14][C:15]([O:17][CH3:18])=[O:16]>CN(C1C=CN=CC=1)C.O1CCOCC1.C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:7][C@H:8]([C@@H:30]([NH:38][C:39](=[O:58])[C@H:40]([CH2:54][C:55](=[O:57])[NH2:56])[NH:41][C:42]([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[N:45]=1)=[O:43])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:9][N:10]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH:11][C:12](=[O:22])[C@H:13]([CH:19]([CH3:20])[CH3:21])[NH:14][C:15]([O:17][CH3:18])=[O:16])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 2

HCID 8855Butyryl chlorideHCID 69782440HCID 69782440, compound

Product 1

HCID 70047688HCID 70047688, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere, a small amount of DMAP and 0.2 ml of butyric acid chloride are added to a solution of 121 mg (0.17 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[phenylmethyl]-2-[N-(methoxycarbonyl)-(L)-valyl]-hydrazine (Example 109) in 3.5 ml of dioxane, 2 ml of methylene chloride and 0.4 ml of pyridine. Dilution of the reaction mixture with methylene chloride, washing with 2 portions of saturated NaHCO3 solution, water and brine, extraction of the aqueous phases with 2 portions of methylene chloride, drying of the organic phases with Na2SO4, concentration by evaporation and column chromatography (SiO2, methylene chloride/methanol 50:1→19:1) yields the title compound: TLC Rf (I')=0.5; tRet (V)=15.6 min.

Workup

  1. washDilution of the reaction mixture with methylene chloride, washing with 2 portions of saturated NaHCO3 solution, water and brine, extraction of the aqueous phases with 2 portions of methylene chloride
  2. dry with materialdrying of the organic phases with Na2SO4, concentration by evaporation and column chromatography (SiO2, methylene chloride/methanol 50:1→19:1)

Sources & evidence

ORD record
ord-0d9cf2c3ed794d60a8ad9a4bbf60ceda
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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