Water → 2-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methyl-butyric acid methyl ester

HRID 910419ノート

反応式

HRID 910419 の反応式
[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:8][C:9](=[O:28])[CH:10]([NH:20][C:21](OC(C)(C)C)=[O:22])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)[CH:5]([CH3:7])[CH3:6].O.CCN(C(C)C)C(C)C.ClC(OC1C=CC=CC=1)=O>C(O)(C(F)(F)F)=O.O1CCOCC1.CN(C=O)C>[CH3:1][O:2][C:3](=[O:29])[CH:4]([N:8]1[C:9](=[O:28])[CH:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[NH:20][C:21]1=[O:22])[CH:5]([CH3:7])[CH3:6]

参加物

8

反応物 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine2 回HCID 666609032-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester2 回

生成物 1

HCID 666606712-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methyl-butyric acid methyl ester

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

The compound obtained in step f above (22f) (900 mg, 1.907 mmol) was stirred in TFA (8 mL) at 0° C. for 5 h, and then concentrated under vacuum. The residue was diluted with CH2Cl2, washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4, concentrated to give the crude product. The obtained crude product was stirred in dioxane (9 mL) and water (1 mL) at 0° C., DIEA (737 mg, 5.72 mmol) and phenyl chloroformate (446 mg, 2.861 mmol) were added, and the mixture was stirred for 1.5 h. The solvent was removed under vacuum; the residue was diluted with EtOAc and washed with brine. The combined organic layers were dried and concentrated to give a yellow oil. The obtained oil was then stirred with DIEA (737 mg, 5.72 mmol) in DMF (10 mL) for 24 h. After general workup, the crude product was purified by silica gel column chromatography to give the title compound as colorless oil (245 mg, 32% from step f.

後処理

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe obtained crude product
  8. customThe solvent was removed under vacuum
  9. additionthe residue was diluted with EtOAc
  10. washwashed with brine
  11. customThe combined organic layers were dried
  12. concentrationconcentrated
  13. customto give a yellow oil
  14. customAfter general workup, the crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-17b3c39006a045f1877730a791a9a9d6
出典データセット
uspto-grants-2011_09
特許番号
US08022092B2

反応ノート

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