Allylamine → (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate

HRID 1039025Notes

Reaction equation

HRID 1039025 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:17]1[C:21]2C=CC=[CH:25][C:20]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C(N)C=C>ClCCl>[CH2:21]([NH:17][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][CH3:14])[CH:20]=[CH2:25]

Participants

7

Reactant 5

HCID 7853AllylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 86654756(S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 500 mL round bottom flask was charged with (S)-2-(tert-butoxycarbonylamino)butanoic acid (5.0 g, 0.025 mol), 1-hydroxybenzotriazole hydrate (3.4 g, 0.025 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (7.2 g, 0.038 mol), and dichloromethane (125 mL). Triethylamine (7.6 mL, 0.055 mol) and allylamine (1.9 g, 0.025 mol) were added and the resulting mixture stirred at room temperature for 22 h. The resulting mixture was then diluted with dichlormethane (300 mL), washed 1× with 1N HCl (200 mL), 1× with 1N NaOH (200 mL), and 1× with water (200 mL). The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo to yield (S)-tert-butyl 1-(allylamino)-1-oxobutan-2-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.15-5.23 (m, 2H), 4.03-4.19 (m, 1H), 3.88-3.92 (m, 2H), 1.82-1.94 (m, 1H), 1.60-1.72 (m, 1H), 1.45 (s, 9H), and 0.96 (t, J=7.4 Hz, 3H).

Workup

  1. washwashed 1× with 1N HCl (200 mL), 1× with 1N NaOH (200 mL), and 1× with water (200 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eeae5466e5084f8381a266aa1c82a80e
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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