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Methanesulfonic Acid → (2S)-2-Benzyloxycarbonylamino-3-(3-(t-butoxycarbonylamino)propanoylamino)propanoic acid methyl ester

HRID 726425
ノート
印刷プレビュー

反応式

HRID 726425 の反応式
[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:5][NH:6][C:7]([O:9]C(C)(C)C)=O.CS(O)(=O)=O.[C:31]([NH:38][CH2:39][CH2:40]C(O)=O)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(#N)C.O.C(N(CC)CC)C.CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:5][NH:6][C:7](=[O:9])[CH2:40][CH2:39][NH:38][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 6395Methanesulfonic AcidHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10831821(S)-Methyl 2-N-Cbz-3-N-Boc-propanoate

生成物 1

HCID 57083146
(2S)-2-Benzyloxycarbonylamino-3-(3-(t-butoxycarbonylamino)propanoylamino)propanoic acid methyl ester

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒

実験手順

The product (6.0 g) obtained in the above (3) is dissolved in acetonitrile (10 ml), and thereto is added dropwise a solution of methanesulfonic acid (8.181 g) in acetonitrile (15 ml) at a temperature below 20° C., and the mixture is stirred at room temperature for 30 minutes. At a temperature below 20° C., to the mixture are added dropwise DMF (20 ml), triethylamine (8.608 g) successively, and the mixture is stirred for 10 minutes. To the mixture are added N-Boc-β-alanine (3.547 g) and HOBT.H2O (3.13 g), and then further added thereto WSC.HCl (3.928 g) at a temperature of from 5° to 10° C., and the mixture is stirred for 30 minutes. The mixture is further stirred at room temperature for 12 hours, and poured into water, and extracted three time with ethyl acetate. The organic layer is washed successively with 1N HCl (twice), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (silica gel; 400 g, solvent; chloroform/acetone=3:1 to 2:1). The fractions containing the title compound are concentrated under reduced pressure to give the title compound (6.974 g).

後処理

  1. stirringthe mixture is stirred for 10 minutes
  2. stirringThe mixture is further stirred at room temperature for 12 hours
  3. extractionextracted three time with ethyl acetate
  4. washThe organic layer is washed successively with 1N HCl (twice), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe desiccant is removed by filtration
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (silica gel; 400 g, solvent; chloroform/acetone=3:1 to 2:1)
  9. additionThe fractions containing the title compound
  10. concentrationare concentrated under reduced pressure

出典と根拠

ORDレコード
ord-7b93134c63144c3684db7c3c0ff4227b
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05707994

反応ノート

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