Acetone → HCID 86705129, compound

HRID 541555Notes

Reaction equation

HRID 541555 reaction equation
[C:1]([O:4][CH2:5]Br)(=[O:3])[CH3:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:32][C@@H:33]([OH:37])[C:34]([OH:36])=[O:35])[NH:23][C:24]([C:26]2[N:27]=[N:28][N:29]([OH:31])[CH:30]=2)=[O:25])=[CH:17][CH:16]=1.CC(C)=O.CCN(CC)CC>>[C:1]([O:4][CH2:5][O:31][N:29]1[CH:30]=[C:26]([C:24]([NH:23][N:22]([CH2:32][C@@H:33]([OH:37])[C:34]([OH:36])=[O:35])[CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:9]3[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=3[Cl:7])=[CH:16][CH:17]=2)=[O:25])[N:27]=[N:28]1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 68536Bromomethyl acetateHCID 67972391HCID 67972391, compound

Product 1

HCID 86705129HCID 86705129, compoundYield 14.5%

Conditions

Temperature
55 °C

Procedure

Bromomethyl acetate (15.3 mg, 100 μmol) was added to a solution of (R)-3-[N-(2′,5′-dichlorobiphenyl-4-ylmethyl)-N′-(1-hydroxy-1H-1,2,3-triazole-4-carbonyl)hydrazino]-2-hydroxypropionic acid (31.2 mg, 66.8 μmol) in acetone (0.5 mL, 6.8 mmol) followed by Et3N (18.6 μL, 134 μmol). The resulting mixture was stirred at 55° C. for 1 hour. The mixture was then concentrated in vacuo to yield a yellow liquid. The crude liquid was purified (preparative scale C18 column chromatography, small column, using 30-90% MeCN in water with 0.05% TFA) to yield the title compound (5.2 mg, purity 96%) as a white solid. MS m/z [M+H]+ calc'd for C22H21Cl2N5O2, 538.08. found 538.1.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customto yield a yellow liquid
  3. customThe crude liquid was purified (preparative scale C18 column chromatography, small column, using 30-90% MeCN in water with 0.05% TFA)

Sources & evidence

ORD record
ord-6761e5bb7020426f826afa03985edb3c
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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