1,2-Dichloroethane → Benzyl 6-[bis(2-tert-butoxy-2-oxoethyl)amino]-6-oxohexanoate

HRID 1488248ノート

反応式

HRID 1488248 の反応式
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:41]([CH2:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CN(C=O)C.O>[C:46]([O:45][C:43](=[O:44])[CH2:42][N:41]([CH2:50][C:51](=[O:52])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])([CH3:49])([CH3:47])[CH3:48]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4393691DI-T-Butyl iminodiacetateHCID 11075409Adipic acid monobenzyl ester

生成物 1

HCID 117995888Benzyl 6-[bis(2-tert-butoxy-2-oxoethyl)amino]-6-oxohexanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 6-(benzyloxy)-6-oxohexanoic acid (1.5 g, 6.35 mmol) in DMF (50 mL) at room temperature was added DIPEA (2.218 mL, 12.70 mmol), HOBt (1.945 g, 12.7 mmol), EDC (2.434 g, 12.7 mmol) and di-tert-butyl 2,2′-iminodiacetate (2.34 g, 9.52 mmol). After stirring at room temperature for 16 hours, the reaction mixture was diluted with H2O (30 mL) and extracted with CH2Cl2 (2×30 mL). The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel (80 g), eluting with 0-40% EtOAc in hexane, to give the title compound. LC-MS Method A: m/e=464.04 [M+1]; Rt=2.47 min. 1H NMR (CDCl3) δ 7.32 (m, 5H), 5.07 (s, 2H), 4.02 (s, 2H), 3.96 (s, 2H), 2.35 (s, 2H), 2.26 (s, 2H), 1.66 (s, 4H), 1.42-1.44 (bs, 18H).

後処理

  1. extractionextracted with CH2Cl2 (2×30 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (80 g)
  6. washeluting with 0-40% EtOAc in hexane

出典と根拠

ORDレコード
ord-a1fc44b91ad547a2ae5093f90d7d7ef2
出典データセット
uspto-grants-2016_08
特許番号
US09427475B2

反応ノート

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