Ammonia → HCID 10626280, compound

HRID 2121246Notes

Reaction equation

HRID 2121246 reaction equation
C[O:2][C:3](=[O:40])[C@H:4]([CH2:36][CH2:37][S:38][CH3:39])[NH:5][C:6](=[O:35])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:10]([CH2:20][O:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].Cl.COC(=O)[C@H](CCSC)N.N>>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH2:20][C:10]2[C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:40])=[O:2])[CH2:36][CH2:37][S:38][CH3:39])=[O:35])=[C:8]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH:9]=2)[CH:23]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 20622805HCID 20622805, compound

Product 1

HCID 10626280HCID 10626280, compound

Procedure

The desired compound was prepared by saponification of the compound of Example 343A, followed by coupling with methionine methyl ester hydrochloride and saponification of the methyl ester as described above. 1H NMR (300 MHz, CDCl3) δ 8.31 (1H, d, J=9 Hz), 8.19 (1H, d, J=3 Hz), 7.90 (1H, d, J=4 Hz), 7.42 (1H, s), 7.40-7.20 (10H, m), 6.07 (1H, d, J=9 Hz), 5.08 (2H, m), 4.62 (1H, m), 2.40 (3H, s), 2.25-2.10 (5H, 2.02 (3H, s), 2.00-1.55 (2H, m). MS (DCI, NH3) m/e 541 (M+H)+. Anal calcd for C32H32N2O4S.0.50H2O: C, 69.92; H, 6.05; N, 5.10. Found: C, 69.94; H, 6.20; N, 4.90.

Sources & evidence

ORD record
ord-b312e67483e141158f8a186e8e4df114
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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