Triphenylphosphine → HCID 178418455、化合物

HRID 1694

反応式

HRID 1694 の反応式
[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]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 178418329HCID 178418329、化合物

生成物 1

HCID 178418455HCID 178418455、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75cd419ae27e4e64877635a7083429d0
出典データセット
uspto-grants-1998_03
特許番号
US05726172

関連ノート

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