Acetyl chloride → HCID 57968592、化合物

HRID 882763ノート

反応式

HRID 882763 の反応式
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:18][C@H:17]([O:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:16][NH:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:34](Cl)(=[O:36])[CH3:35]>C1COCC1.C([O-])(O)=O.[Na+]>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:18][C@H:17]([O:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[CH2:16][N:15]3[C:34](=[O:36])[CH3:35])=[O:13])[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 44601159HCID 44601159、化合物

生成物 1

HCID 57968592HCID 57968592、化合物収率 61%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of (2S,4S)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(4-fluoro-phenoxy)-pyrrolidine (102 mg, 0.85 mmol) and Et3N (0.197 mL) in THF (2.82 mL) was added acetyl chloride (60 μL, 0.85 mmol). After 48 h, the mixture was diluted with saturated (satd.) aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried and evaporated. The residue was purified by FCC, followed by reverse phase HPLC (5-99% CH3CN/20 mM NH4OH) to give the desired product (69 mg, 61%). MS (ESI): mass calcd. for C22H30FN3O3, 403.23; m/z found, 404.3 [M+H]+. 1H NMR (CDCl3): 7.02-6.92 (m, 2H), 6.87-6.77 (m, 2H), 4.92-4.79 (m, 2H), 4.12-3.96 (m, 1H), 3.84-3.47 (m, 5H), 2.92-2.77 (m, 1H), 2.66-2.51 (m, 2H), 2.50-2.41 (m, 2H), 2.39-2.30 (m, 1H), 2.22-2.12 (m, 1H), 2.10 (d, J=2.1 Hz, 3H), 2.07-1.98 (m, 2H), 1.92-1.72 (m, 4H), 1.71-1.54 (m, 2H).

後処理

  1. extractionextracted with CH2Cl2 (3×)
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-4fe53906cbd240dfa9d11ef140beed00
出典データセット
uspto-grants-2012_08
特許番号
US08236792B2

反応ノート

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