Ammonia → HCID 10576186, compound

HRID 2121241Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12](C(O)=O)=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH:10]=2)[CH:2]=1.N[C@H](C(O)=O)CCSC.Cl.C[O:36][C:37](=[O:59])[C@H:38]([CH2:55][CH2:56][S:57][CH3:58])[NH:39][C:40](=[O:54])C1C=CC(N)=CC=1C1C=CC=CC=1.N>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:40]([NH:39][C@H:38]([C:37]([OH:59])=[O:36])[CH2:55][CH2:56][S:57][CH3:58])=[O:54])=[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH:10]=2)[CH:2]=1

Participants

Reactant 4

HCID 222Ammonia

HCID 6137L-Methionine

HCID 23436443HCID 23436443, compound

HCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

Product 1

HCID 10576186HCID 10576186, compound

Procedure

The desired compound was prepared by coupling of 4-(3-pyridylthiomethyl)-2-(2-methylphenyl)benzoic acid with methionine phenylsulfonimide hydrochloride using the procedure used in step C of the preparation of compound 8. 1H NMR (300 MHz, CDCl3) δ 8.50 (m, 2H), 8.02 (m, 2H), 7.93 (t, 1H), 7.62 (m, 2H), 7.51 (m, 2H), 7.17-7.42 (m, 5H), 7.09 (m, 2H), 5.71 (d, 1H), 4.40 (m, 1H), 4.13 (s, 2H), 1.86-2.13 (m, 8H), 1.71 (m, 1H), 1.25 (m, 1H). MS (CI, NH3) m/e 606, 225. Anal calcd for C31H31N3O4S3 1.53 TFA: C, 52.43; H, 4.20; N, 5.39. Found: C, 52.42; H, 4.14; N, 5.43.

Sources & evidence

ORD record: ord-cd0723e755554e749e8677dbac939a1d
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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