1-Hydroxybenzotriazole → HCID 86757773, compound

HRID 1699127Notes

Reaction equation

HRID 1699127 reaction equation
[CH:1]1C=CC2N(O)N=NC=2C=1.[C:11]([O:15][C:16]([NH:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl.CN(C)CCCN=C=NCC.Cl.[NH2:40][CH:41]([CH2:47][CH:48]=[CH2:49])[CH2:42][C:43]([O:45]C)=[O:44].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][N:18]([C:16]([O:15][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:17])[C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH:21]([CH3:22])[CH3:23].[NH2:40][CH:41]([CH2:47][CH:48]=[CH2:49])[CH2:42][C:43]([O-:45])=[O:44]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18323201HCID 18323201, compound

Product 1

HCID 86757773HCID 86757773, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (255 mg) was added to a solution of N-(t-butoxycarbonyl)leucine (297 mg) in DMF (5 ml), followed by 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (273 mg) and the solution stirred for 15 min. Methyl 3-amino-5-hexenoate hydrochloride (185 mg) was dissolved in DMF (5 ml) and triethylamine (140 μl) and the resultant solution added to the solution of the N-(t-butoxycarbonyl)leucine activated ester followed by diisopropylethylamine (100 μl). The mixture was stirred overnight at ambient temperature. The mixture was added to ethyl acetate(30 ml), washed with water (2×5 ml), 5% citric acid (3 ml), water (5 ml), saturated sodium bicarbonate solution (5 ml), water (5 ml), saturated brine (5 ml), dried (MgSO4) and evaporated to give methyl N-(t-butoxycarbonyl)leucine-3-amino-5-hexenoate (335 mg); NMR (CDCl3): 0.9 (6H, d), 1.4(10H, m), 1.6-1.8 (2H, m), 2.2-2.3 (2H,m), 2.5(2H,d), 3.6(3H,s), 4.0-4.1(1H, m), 4.2-4.3 (1H,m), 4.8-4.9(1H,b), 5.0-5.1 (2H,d), 5.6-5.8 (1H,m), 6.5-6.6(1H,m): m/Z 357 (M+H)

Workup

  1. stirringThe mixture was stirred overnight at ambient temperature
  2. washwashed with water (2×5 ml), 5% citric acid (3 ml), water (5 ml), saturated sodium bicarbonate solution (5 ml), water (5 ml), saturated brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-77c769135e144b28b782aa7f2d1d0d5c
Source dataset
uspto-grants-2002_02
Patent number
US06344570B1

Reaction notes

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