Water → Methyl 3-aminopropanoate hydrochloride

HRID 864849Notes

Reaction equation

HRID 864849 reaction equation
[ClH:1].Cl.N1C=C[C:6]([CH:9]2[CH2:14]N[CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22]C)=[O:20])=CC=1.[CH3:24][N:25](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[CH:15]([N:10]([CH:9]([CH3:6])[CH3:14])[CH2:11][CH3:12])([CH3:16])[CH3:24].[ClH:1].[NH2:25][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131719611HCID 131719611, compound

Product 2

HCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 189 (i), the product of Example 196 (840 mg), HBTU (950 mg), HOBt.H2O (380 mg), DMF (10 ml), diisopropylethylamine (2.6 ml) and methyl 3-aminopropionate, hydrochloride (280 mg) gave, after purification by flash chromatography on neutral alumina, eluting solvent ethyl acetate/methanol, 50:1 to 4:like title compound (303 mg) as a white crystalline solid: m.p. 118°-122° C.; NMR (d6 -DMSO) δ1.45 (4H, m), 2.05 (2H, t), 2.27 (2H, t), 2.42 (6H, m), 3.26 (6H, m), 3.58 (3H, s), 6.78 (2H, m), 7.83 (1H br, t), 8.12 (2H, m); m/Z 349 (M+H)+ ; calculated for C18H28N4O3 : C, 62.0%; H, 8.1%; N, 16.1%; found: C, 62.2%; H, 8.4%; N, 16.0%.

Sources & evidence

ORD record
ord-81b84ab18ecf4d918e834595333b27ca
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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