Acetone → HCID 86705130, compound

HRID 541556Notes

Reaction equation

HRID 541556 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:35][C@@H:36]([OH:40])[C:37]([OH:39])=[O:38])[NH:26][C:27]([C:29]2[N:30]=[N:31][N:32]([OH:34])[CH:33]=2)=[O:28])=[CH:20][CH:19]=1.CC(C)=O.CCN(CC)CC>>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]([CH2:35][C@@H:36]([OH:40])[C:37]([OH:39])=[O:38])[NH:26][C:27]([C:29]2[N:30]=[N:31][N:32]([O:34][CH2:2][C:3]3[O:4][C:5](=[O:9])[O:6][C:7]=3[CH3:8])[CH:33]=2)=[O:28])=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 67972391HCID 67972391, compound

Product 1

HCID 86705130HCID 86705130, compoundYield 25.9%

Conditions

Temperature
65 °C

Procedure

4-Chloromethyl-5-methyl-1,3-dioxol-2-one (14.9 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 65° C. for 2 hours. 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 (10.0 mg, purity 99%) as a white solid. MS m/z [M+H]+ calc'd for C24H21Cl2N5O8, 578.08. found 578.1.

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-97796307b4404737a0b727095ef2f0f6
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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