Ethyl bromoacetate → HCID 67458407, compound

HRID 553813Notes

Reaction equation

[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:38])[C@@H:13]([NH:17][C:18]([C:20]2[CH:25]=[C:24]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:23]=[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:21]=2)=[O:19])[CH2:14][CH2:15][OH:16])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:49]([O:51][C:52](=[O:55])[CH2:53]Br)[CH3:50]>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:38])[C@@H:13]([NH:17][C:18]([C:20]2[CH:25]=[C:24]([O:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[N:23]=[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:21]=2)=[O:19])[CH2:14][CH2:15][O:16][CH2:53][C:52]([O:51][CH2:49][CH3:50])=[O:55])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

4-{(S)-2-[(6-cyclopentyloxy-2-phenyl-pyrimidine-4-carbonyl)-amino]-4-hydroxy-butyryl}-piperazine-1-carboxylic acid ethyl ester (16.8 mg) was dissolved in THF (1 ml) under argon and cooled to 0° C. A solution of potassium bis-(trimethylsilyl)-amide (0.5 M in toluene, 8 μl) and, 5 min later, ethylbromoacetate (5 μl) were added. The mixture was stirred at 0° C. for 1 h and evaporated off. The residue was taken up in water and extracted twice with EA. The org. layers were washed with water, a NaCl solution, dried (Na2SO4) and evaporated off to give 19 mg of the desired compound.

Workup

customevaporated off
extractionextracted twice with EA
washlayers were washed with water
dry with materiala NaCl solution, dried (Na2SO4)
customevaporated off

Sources & evidence

ORD record: ord-69a294d6c746478c8c7bcaf3d5ed4263
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048881B2

Reaction notes

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