Hydrochloric Acid → HCID 86619839, compound

HRID 1994298Notes

Reaction equation

HRID 1994298 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[CH2:17][CH2:16][N:15]([C@H:18]([CH:26]([CH3:28])[CH3:27])[C:19](OC(C)(C)C)=[O:20])[C:14]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCN(C(C)C)C(C)C.ClC(OCC)=O.C[Si](C)(C)[O:57][NH2:58].Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[CH2:17][CH2:16][N:15]([C@H:18]([CH:26]([CH3:27])[CH3:28])[C:19]([NH:58][OH:57])=[O:20])[C:14]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 86619837HCID 86619837, compound

Product 1

HCID 86619839HCID 86619839, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (102 mg; 0.23 mmol) was dissolved in CH2Cl2 (2 ml) and cooled to 0° C. Trifluoroacetic acid (TFA; 1 ml) was added, and the mixture was stirred for 2 h. The solvents were removed under reduced pressure, and the residue was taken up in tetrahydrofuran (THF; 2 ml). DIEA (0.16 ml; 0.93 mmol) and ethyl chloroformate (67 μl; 0.69 mmol) were added. After stirring at RT for 2 h, O-trimethylsilylhydroxylamine (0.10 ml; 1.39 mmol) was added. The mixture was stirred for 15 h, HCl (6N, 0.30 ml) was added, and then the solvents were removed under reduced pressure. Purification of the residue by preparative HPLC resulted in (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide (8 mg, 0.02 mmol). MS: 398.15 (M+H); Rt: 1.46 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. customThe solvents were removed under reduced pressure
  2. stirringAfter stirring at RT for 2 h
  3. stirringThe mixture was stirred for 15 h
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by preparative HPLC

Sources & evidence

ORD record
ord-7ae74b3e1a634cbd9bf0f55454dd12a9
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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