Triphenylphosphine → HCID 178418455, 화합물

HRID 1694

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HRID 1694 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]([NH:40][C@H:41]1[CH2:46][CH2:45][C@H:44](O)[CH2:43][CH2:42]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].N(C(OCC)=O)=N[C:50](OCC)=[O:51]>C1COCC1>[C:33]([NH:40][C@H:41]1[CH2:46][CH2:45][C@@H:44]([C:50]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:51])[CH2:43][CH2:42]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 178418329HCID 178418329, 화합물

생성물 1

HCID 178418455HCID 178418455, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (1.09 g, 6.0 mmol) in dry THF (7 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the solution was cooled to 0° C. A 4.0 mL volume of N-Boc-trans-1-amino-4-cyclohexanol (1 g, 4.0 mmol) and diethyl azodicarboxylate (945 μL, 6.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 70:30 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate.

후처리

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-75cd419ae27e4e64877635a7083429d0
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

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