N-(tert-butoxycarbonyl)glycine → methyl N-(tert-butoxycarbonyl)glycylglycinate

HRID 2370890ノート

反応式

HRID 2370890 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C(N(CC)C(C)C)(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:18][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

参加物

7

反応物 5

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 637608methyl N-(tert-butoxycarbonyl)glycylglycinate収率 70%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

N-tert-butoxycarbonyl glycine (10.57 g, 60.33 mmol) and glycine methyl ester hydrochloride (7.58 g, 60.4 mmol) were dissolved in DMF (60 mL). N,N-diisopropylethyl amine (7.80 g, 60.4 mmol) and HOBt hydrate (9.24 g, 60.3 mmol) dissolved in DMF (40 mL) were added. The solution was cooled to 0° C. (icebath) and EDC hydrochloride (12.72 g, 66.35 mmol) added in small portions. The reaction mixture was stirred for 15 hours before the solvent was evaporated. The residue was taken up in EtOAc (300 mL) and washed with 2 M aqueous H2SO4 (3×50 mL), 7.5% (w/w) aqueous K2CO3 (3×50 mL) and saturated brine (50 mL). The solution was dried with anhydrous MgSO4 and the solvent evaporated affording the title compound as a clear liquid (10.34 g, 70%) with spectral characteristics in accordance with literature data8; δH (300 MHz; d6-DMSO) 8.17 (1H, t, J 6, NH(Gly2)), 6.97 (1H, t, J 6, NH(Gly1)), 3.85 (2H, d, J 6, CαH2(Gly2)), 3.62 (3H, s, OCH3), 3.57 (2H, d, J 6, CαH2(Gly1)), 1.38 (9H, s, (CH3)3); δC (75 MHz; d6-DMSO) 170.2, 169.9, 155.7, 78.0, 51.6, 42.9, 40.4, 28.1; m/z (ESI) 269.1110 ([M+Na]+; C10H18N2O5 requires 269.1113)

後処理

  1. additionwere added
  2. additionadded in small portions
  3. customwas evaporated
  4. washwashed with 2 M aqueous H2SO4 (3×50 mL), 7.5% (w/w) aqueous K2CO3 (3×50 mL) and saturated brine (50 mL)
  5. dry with materialThe solution was dried with anhydrous MgSO4
  6. customthe solvent evaporated

出典と根拠

ORDレコード
ord-65b486ec0b4945e58d6f98663b7bdd50
出典データセット
uspto-grants-2014_04
特許番号
US08710008B2

反応ノート

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