Gamma-Aminobutyric Acid → HCID 54691732, compound

HRID 2214672Notes

Reaction equation

HRID 2214672 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[S:20]([CH3:22])=[O:21])[CH3:11])=[O:9])[C:4](=[O:23])O1.[CH2:25]=O.[NH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32]>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:10]([CH3:11])[C:8]([C:7]2[CH2:25][N:27]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:4](=[O:23])[C:5]=2[OH:6])=[O:9])=[C:14]([S:20]([CH3:22])=[O:21])[CH:15]=1

Participants

4

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 712FormaldehydeHCID 69655562HCID 69655562, compound

Product 1

HCID 54691732HCID 54691732, compoundYield 18%

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfinyl-benzyl)-N-methyl-acetamide was reacted with paraformaldehyde and 4-amino-butyric acid as described in Method 44B to give the title compound as a colorless oil (0.015 g, 18% yield). 1HNMR (300 MHz, CDCl3) δ: 7.76 (1H, dd, J=8.05, 2.20 Hz), 7.34 (1H, dd, J=8.41, 5.12 Hz), 7.19 (1H, td, J=8.05, 2.56 Hz), 4.85 (2H, d, J=15.01 Hz), 4.18 (2H, s), 3.58 (2H, t, J=5.86), 3.01 (3H, s), 2.76 (3H, s), 2.39 (2H, t, J=5.86 Hz), 1.95 (2H, t, J=6.22 Hz).

Sources & evidence

ORD record
ord-b90d1b4235a14b81bce1ef09a643a04a
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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