反応式
[N:1]1([C:9]([O:11][CH2:12][CH:13]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=O.S(Cl)(Cl)=O.[Br:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[C:33]([F:38])[CH:32]=1.N1C=CC=CC=1>ClCCl>[CH:24]1[C:25]2[CH:13]([CH2:12][O:11][C:9]([N:1]3[CH2:8][CH2:7][CH2:6][C@@H:2]3[C:3](=[O:5])[NH:35][C:34]3[CH:36]=[CH:37][C:31]([Br:30])=[CH:32][C:33]=3[F:38])=[O:10])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][CH:23]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
Fmoc-D-Pro (1.2 g, 3.56 mmol) was suspended in 10 mL dry dichloromethane (DCM), cooled in an ice water bath, and then thionyl chloride (0.78 mL, 10.7 mmol) was added slowly. After addition was complete, the ice water bath was removed and the reaction was stirred at ambient temperature overnight. The solution was concentrated to dryness. The oil was redissolved in 20 mL dry DCM under an Ar atmosphere, and 4-bromo-2-fluoroaniline (0.81 g, 4.3 mmol) was added, followed by dry pyridine (0.87 mL, 10.7 mmol). The mixture was stirred at ambient temperature for 4 hours, then concentrated. The residue was redissolved in 100 mL EtOAc, washed with 1M HCl (3×50 mL), brine (2×50 mL), dried with MgSO4, filtered and concentrated to yield the title product as a sticky oil. (1.8 g, 99%) APCI (AP+): 509.2, 511.2 (M+H)+.
後処理
- temperaturecooled in an ice water bath
- additionAfter addition
- customthe ice water bath was removed
- concentrationThe solution was concentrated to dryness
- additionwas added
- stirringThe mixture was stirred at ambient temperature for 4 hours
- concentrationconcentrated
- dissolutionThe residue was redissolved in 100 mL EtOAc
- washwashed with 1M HCl (3×50 mL), brine (2×50 mL)
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-27ec977d87b443c3923f8670a7c1734f
- 出典データセット
- uspto-grants-2006_04
- 特許番号
- US07030141B2
関連ノート
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