Benzyl chloroformate → 3-(N-Carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine

HRID 1004839ノート

反応式

HRID 1004839 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:25])[CH2:11][N:10]([CH:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[C:4]([F:26])[CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>CC(C)=O.O>[C:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:25])[CH2:9][N:10]([CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:11]2)=[C:4]([F:26])[CH:3]=1)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 226257053-(4-Amino-2-fluorophenyl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine

生成物 1

HCID 226256753-(N-Carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

To a solution of 3-(4-amino-2-fluorophenyl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine (Example 81, Step 1, 5.10 g, 14.7 mmol) in acetone (75 mL) was added a solution of sodium bicarbonate (2.52 g, 30.0 mmol) in water (40 mL) to give a creamy suspension. Benzyl chloroformate (2.57 g, 15.1 mmol) was added and stirring continued overnight. The suspension was filtered and the acetone evaporated. The residue was partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered and evaporated to leave an amber foam. Chromatography over silica gel (150 g, 40-60 μM) eluting with 1-2% methanol-methylene chloride gave the title compound as a cream foam. HRMS: meas. 483.2087, theory 483.2084.

後処理

  1. customto give a creamy suspension
  2. filtrationThe suspension was filtered
  3. customthe acetone evaporated
  4. customThe residue was partitioned between ethyl acetate (200 mL) and water (50 mL)
  5. washThe organic layer was washed with brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto leave an amber foam
  10. washChromatography over silica gel (150 g, 40-60 μM) eluting with 1-2% methanol-methylene chloride

出典と根拠

ORDレコード
ord-0a76d62fa70548af81643bf5253dcb0b
出典データセット
uspto-grants-2000_04
特許番号
US06051716

反応ノート

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