4-(Heptyloxy)benzoyl chloride → 4-(2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

HRID 1889154ノート

反応式

HRID 1889154 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:27][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[CH:22][C:23]=2[O:28][CH3:29])=[O:43])=[CH:45][CH:46]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

参加物

4

反応物 2

HCID 27241824-(Heptyloxy)benzoyl chlorideHCID 58545693Tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate

生成物 1

HCID 585458034-(2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Prepared using General Procedure 3: To a stirred solution of tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-methoxyphenyl)propanoate INT-2 (4.7 g, 11.71 mmol) and TEA (3.05 mL, 21.07 mmol) in DCM (50 mL) at 0° C. was added 4-(heptyloxy)benzoyl chloride (2.95 mL, 12.29 mmol) dropwise. After warming to room temperature and stirring for 10 min, the mixture was quenched with saturated aqueous NaHCO3 (50 mL) and water (50 mL). The organic layer was dried over MgSO4 and concentrated. The product was purified by chromatography (EA/hexanes) to afford 5.46 g (75%) of 4-(2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-3. LCMS-ESI (m/z) calculated for C36H45NO8: 619; found 564 [M+H-tBu]+, tR=3.22 min (Method 4).

後処理

  1. customPrepared
  2. customthe mixture was quenched with saturated aqueous NaHCO3 (50 mL) and water (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-2421371175614b8c83d39c36f1287c3b
出典データセット
uspto-grants-2013_08
特許番号
US08501982B2

反応ノート

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