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

HRID 473511

반응식

HRID 473511 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-62cd3eea51ac4edcad431c8641206e90
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633322B2

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