Benzyl 3-aminopropanoate → HCID 19037105, compound

HRID 976490Notes

Reaction equation

[O:1]=[C:2]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])/[C:3](/[CH2:17][S:18][C:19](=[O:21])[CH3:20])=[CH:4]/[C:5]1C=C[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.NCCC(OCC1C=CC=CC=1)=O>>[O:1]=[C:2]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])/[C:3](/[CH2:17][S:18][C:19](=[O:21])[CH3:20])=[CH:4]/[C:5]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 1116164Benzyl 3-aminopropanoate

HCID 19037106HCID 19037106, compound

Product 1

HCID 19037105HCID 19037105, compoundYield 57%

Procedure

The above (Z) acid is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 57% (after flash chromatography, eluent ether/petroleum ether 60/40). m.p. 81° C. IR (nujol): 3290, 1740, 1695, 1640, 1620 cm-1 1H NMR (CDCl3 /TMS): 8.20 (s, 1H); 8.00 to 7.70 (m, 3H); 7.65 to 7.00 (m, 10H); 5.20 (s, 2H); 3.90 (s, 2H); 3.65 to 3.45 (m, 2H); 2.65 (t, 2H, J=6 Hz); 2.35 (s, 3H). Microanalysis: C26H25O4NS Calc. % C=69.78 H=5.63 N=3.13 Found. % C=69.86 H=5.68 N=3.17

Sources & evidence

ORD record: ord-43b3ee990c144f66acaed09237d57bda
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612371

Reaction notes

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