methyl (2S)-2-amino-4-(methylsulfanyl)butanoate → HCID 54128509, compound

HRID 2121200Notes

Reaction equation

HRID 2121200 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:27][O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH2:31]>>[CH3:27][O:28][C:29](=[O:36])[C@H:30]([CH2:32][CH2:33][S:34][CH3:35])[NH:31][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 10570985HCID 10570985, compound

Product 1

HCID 54128509HCID 54128509, compound

Procedure

The desired compound was prepared from 4-(3-pyridylsulfonylmethyl)-2-phenylbenzoic acid methyl ester by saponification of the methyl ester using the procedure of Example 228D, and coupling with methionine methyl ester according to the procedure of Example 186C. mp 152-154° C. 1H NMR (300 MHz, CDCl3) δ 8.95 (d, 1H), 8.87 (dd, 1H), 7.94 (ddd, 1H), 7.66 (d, 1H), 7.43 (m, 4H), 7.30 (m, 2H), 7.21 (dd, 1H), 7.10 (d, 1H), 5.91 (bd, 1H), 4.66 (ddd, 1H), 4.42 (s, 2H), 3.68 (s, 3H), 2.08 (t, 2H), 2.02 (s, 3H), 1.93 (m, 1H), 1.75 (m, 1H). MS (CI NH3) m/e 516 (M+NH4)+, 499 (M+H)+. Anal calc' for C25H26N2O5S2: C, 60.22; H, 5.25; N, 5.62. Found: C, 60.28; H, 4.94; N, 5.56.

Sources & evidence

ORD record
ord-9a8aeffce0f448e882e85387ac9a707f
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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