N-Carbethoxyphthalimide → (S)-2-phthalimido-3-phenylpropionamide

HRID 1417367Notes

Reaction equation

C(N1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])(OCC)=O.Cl.[NH2:18][C@H:19]([C:27]([NH2:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:7]1(=[O:16])[N:18]([C@@H:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]([NH2:29])=[O:28])[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]12

Participants

Reactant 2

HCID 31187N-Carbethoxyphthalimide

HCID 11953719Phenylalanine amide hydrochloride

Product 1

HCID 765708(S)-2-phthalimido-3-phenylpropionamide

Procedure

By following the procedure of Example 19 but employing N-carbethoxyphthalimide and (S)-phenylalaninamide hydrochloride, there is obtained (S)-2-phthalimido-3-phenylpropionamide which can be recrystallized from ethanol to afford white crystals: mp 211°-215° C.; 1H NMR (DMSO-d6) δ 7.92 (s, 5 H, Ph), 7.72, 7.33 (2 s, 2 H), 7.2-7.0 (m, 4 H, Ar), 4.92 (dd, 1H, J=12,4.5 Hz), 3.52 (dd, 1 H, J=4.3, 13.9), 3.35 (dd, 1 H, J=12, 13.9); 13C NMR (DMSO-d6) δ 169.6, 167.4, 137.7, 134.3, 131.2, 128.5, 128.1, 126.3, 122.9, 54.2, 33.7.

Sources & evidence

ORD record: ord-6126ed0b455e4ef184c7f94d2cdbcb88
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05877200

Reaction notes

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