Diisopropylethylamine → Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid benzyl ester

HRID 576557ノート

反応式

HRID 576557 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]([NH:5]CCNC)=[O:4].CCN(C(C)C)C(C)C.[CH2:21]([O:28][C:29]([N:31]1[C:35](=O)[CH2:34]C[C:32]1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29](=[O:30])[N:31]([CH3:32])[CH2:35][CH2:34][NH:5][C:3](=[O:4])[C:2]([F:11])([F:10])[F:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 107022842,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide

生成物 1

HCID 58480374Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid benzyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of compound A (88.2 g, 311 mmol) and DIEA (54.1 mL, 311 mmol) in THF (350 mL) was cooled in an ice bath, followed by the addition of a solution of N-(benzyloxycarbonyl)succinimide (76.6 g, 307 mmol) in THF (150 mL) drop wise over the period of 20 min. The temperature of the reaction mixture was raised to ambient temperature and stirring was continued for an additional 30 min. Solvents were then evaporated and the resulting residue was dissolved in EtOAc (600 mL). The organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL). The organic layer was evaporated to provide compound B as yellowish oil. LC-MS [M+H] 305.1 (C13H15F3N2O3+H, calc: 305.3). Compound B was used directly in the next reaction without purification as a MeOH solution.

後処理

  1. customSolvents were then evaporated
  2. dissolutionthe resulting residue was dissolved in EtOAc (600 mL)
  3. extractionThe organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL)
  4. customThe organic layer was evaporated

出典と根拠

ORDレコード
ord-667c560b500547eba3fb5011abfbfb01
出典データセット
uspto-grants-2015_05
特許番号
US09040032B2

反応ノート

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