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

HRID 473511Notes

Reaction equation

HRID 473511 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-62cd3eea51ac4edcad431c8641206e90
Source dataset
uspto-grants-2014_01
Patent number
US08633322B2

Reaction notes

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