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

HRID 2075812노트

반응식

HRID 2075812 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-29521ce983b04b51a0a5ab8b1d9bc0fa
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923433B2

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