Acetic Acid → HCID 178447345, compound

HRID 1988280Notes

Reaction equation

HRID 1988280 reaction equation
[NH:1]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:2]([C:11]([N:13]([CH3:37])[C@H:14]([C:18]([NH:20][C@H:21]([C:34]([NH2:36])=O)[CH2:22][C:23]1[CH:28]=[CH:27][C:26](O)=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[CH3:45]OC(OC)N(C)C.C(O)(=O)C.[OH2:57].[NH2:58][NH2:59]>C(Cl)Cl.O1CCOCC1.O>[C:30]([C:25]1[CH:24]=[C:23]([CH2:22][CH:21]([NH:20][C:18](=[O:19])[CH:14]([N:13]([C:11](=[O:12])[CH:2]([NH:1][C:38]([O:40][C:41]([CH3:43])([CH3:44])[CH3:42])=[O:39])[CH2:3][C:4]2[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=2)[CH3:37])[CH:15]([CH3:16])[CH3:17])[C:34]2[NH:36][CH:45]=[N:58][N:59]=2)[CH:28]=[CH:27][C:26]=1[OH:57])([CH3:32])([CH3:31])[CH3:33]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 131727517Boc-Phe(4-F)-N-Me-Val-Tyr(3-tBu)-NH2

Product 1

HCID 178447345HCID 178447345, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Boc-Phe(4-F)-N-Me-Val-Tyr(3-tBu)-NH2 (400 mg, 0.651 mmol) in methylene chloride (6.5 ml), dimethylformamide dimethylacetal (0.26 ml, 1.954 mmol) was added at room temperature. The mixture was stirred for 30 min. and evaporated to remove the solvent under reduced pressure. To a solution of the thus obtained residue in dioxane (6.5 ml), acetic acid (2 ml) and hydrazine monohydrate (48 μl, 0.977 mmol) were added at room temperature. The mixture was stirred for 40 min., mixed with water and filtered to collect the precipitated solid. The thus obtained solid was subjected to silica gel column chromatography (developing solvent: ethyl acetate), giving 2-((2-t-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methylbutyric acid 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-triazol-2-yl)ethylamide (384 mg, 93%).

Workup

  1. customevaporated
  2. customto remove the solvent under reduced pressure
  3. stirringThe mixture was stirred for 40 min.
  4. filtrationfiltered
  5. customto collect the precipitated solid

Sources & evidence

ORD record
ord-bbd6ed71b9e446b298b4db74eff28973
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

Loading…