Triethylamine → (S)-N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide

HRID 473511

反応式

HRID 473511 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]([NH:5][C@@H:6]([CH2:10][CH3:11])[C:7]([OH:9])=O)=[O:4].O.O[N:16]1[C:20]2C=[CH:22][CH:23]=[CH:24][C:19]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C(N)CCC#C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:20]([NH:16][C:7](=[O:9])[C@@H:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:13])[F:12])[CH2:10][CH3:11])[CH2:19][CH2:24][C:23]#[CH:22]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 641001Pent-4-yn-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 79006992(S)-(+)-2-trifluoroacetylaminobutyric acid

生成物 1

HCID 86653105(S)-N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A 500 mL round bottom flask was charged with 2-(S)-(2,2,2-trifluoroacetylamino)-butyric acid (5.0 g, 0.025 mol), 1-hydroxybenzotriazole hydrate (4.5 g, 0.033 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.4 g, 0.033 mol), 4-(dimethylamino)pyridine (0.02 g, 0.163 mmol), and dimethylformamide (95 mL). To the resulting mixture was then added triethylamine (10.6 mL, 0.076 mol) and pent-4-yn-1-amine (2.7 g, 0.033 mol). The resulting mixture was stirred at room temperature for 22 h, then concentrated in vacuo and the resulting residue purified via flash silica gel chromatography (Analogix IF-280, SF65-400 g column, gradient 90:10-40:60 Heptane:EtOAc) to yield (S)—N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide. 1H NMR (300 MHz, CDCl3) δ 4.46-4.53 (m, 1H), 3.32-3.48 (m, 2H), 2.23-2.29 (m, 2H), 2.00 (s, 1H), 1.86-1.98 (m, 2H), 1.71-1.83 (m, 2H), and 0.91-0.98 (m, 3H).

後処理

  1. concentrationconcentrated in vacuo
  2. customthe resulting residue purified via flash silica gel chromatography (Analogix IF-280

出典と根拠

ORDレコード
ord-62cd3eea51ac4edcad431c8641206e90
出典データセット
uspto-grants-2014_01
特許番号
US08633322B2

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