Sodium Cyanate → (S)-methyl 2-[4-(carbamoylamino)phenyl]propanoate

HRID 468584Notes

Reaction equation

HRID 468584 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=S)[NH2:2].NC1C=CC([C@H](C)C(OC)=[O:26])=CC=1.[O-]C#N.[Na+]>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:26])[NH2:2]

Participants

4

Reactant 3

HCID 517096Sodium CyanateHCID 57026624methyl (2S)-2-(4-aminophenyl)propanoateHCID 86657117(S)-methyl 2-[4-(carbamothioylamino)phenyl]propanoate

Product 1

HCID 67304177(S)-methyl 2-[4-(carbamoylamino)phenyl]propanoate

Procedure

Following the same procedure described for (S)-methyl 2-[4-(carbamothioylamino)phenyl]propanoate and starting from methyl (2S)-2-(4-aminophenyl)propanoate (98 mmol) and sodium cyanate (128 mmol), after workup (S)-methyl 2-[4-(carbamoylamino)phenyl]propanoate was isolated as white solid (59%). 1H-NMR (CDCl3): δ 8.90 (bs, 1H, CONH), 7.55 (d, 2H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 6.50 (bs, 2H, CONH2), 3.75 (m, 1H), 3.60 (s, 3H), 1.50 (d, 3H, J=7 Hz).

Sources & evidence

ORD record
ord-f59013d3a5f540aab439632de2f152e2
Source dataset
uspto-grants-2014_01
Patent number
US08624036B2

Reaction notes

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