4-Methylmorpholine → 3-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

HRID 2075812ノート

反応式

HRID 2075812 の反応式
[C:1](C(CCCCCCCCCN)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN=C=N[CH2:27][CH2:28][CH2:29]N(C)C.[CH:33]1[CH:34]=[CH:35][C:36]2N(O)N=[N:39][C:37]=2[CH:38]=1.[C:43]([O:47][C:48](=[O:66])[CH2:49][CH:50]([NH2:65])[CH:51]([OH:64])[CH2:52][O:53][C:54]1[C:59]([F:60])=[C:58]([F:61])[CH:57]=[C:56]([F:62])[C:55]=1[F:63])([CH3:46])([CH3:45])[CH3:44].CN1CC[O:71][CH2:70][CH2:69]1>CN(C=O)C.CCOC(C)=O>[C:43]([O:47][C:48](=[O:66])[CH2:49][CH:50]([NH:65][C:70](=[O:71])[CH2:69][CH2:29][CH2:28][CH2:27][CH2:36][CH2:35][CH2:34][CH2:33][CH2:38][CH2:37][NH:39][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH:51]([OH:64])[CH2:52][O:53][C:54]1[C:55]([F:63])=[C:56]([F:62])[CH:57]=[C:58]([F:61])[C:59]=1[F:60])([CH3:46])([CH3:44])[CH3:45]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54758946Boc-11-amino-undecanoic acidHCID 750793883-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

生成物 1

HCID 866130763-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester収率 24%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Boc-11-amino-undecanoic acid (115 mg, 0.38 mmol, 1.2 equiv), EDAC (91 mg, 0.48 mmol, 1.5 equiv), and HOBt (65 mg, 0.48 mmol, 1.5 equiv) in DMF (10 mL) were added to a dry round bottom flask equipped with a magnetic stir bar. Composition 14 (115 mg, 0.32 mmol) and N-methylmorpholine (twice distilled, 0.14 mL, 0.96 mmol, 3.0 equiv) dissolved in minimal quantity of DMF were added with constant stirring. The colorless solution slowly turned yellow as the reaction proceeded. The reaction was allowed to stir for 18 h, then EtOAc (20 mL) was added and the organic layer was washed with saturated NaHCO3 (20 mL), H2O (20 mL) and brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The resulting oil was purified via column chromatography (silica gel, 1:1, hexane/EtOAc) to give 15 (56 mg, 0.088 mmol, 24% yield) as a clear, thick oil. ESMS: 637.6 (M+H), 659.2 (M+Na+).

後処理

  1. customequipped with a magnetic stir bar
  2. additionwere added with constant stirring
  3. washthe organic layer was washed with saturated NaHCO3 (20 mL), H2O (20 mL) and brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified via column chromatography (silica gel, 1:1, hexane/EtOAc)

出典と根拠

ORDレコード
ord-29521ce983b04b51a0a5ab8b1d9bc0fa
出典データセット
uspto-grants-2011_04
特許番号
US07923433B2

反応ノート

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