L-Methionine → HCID 18392924, compound

HRID 1739155Notes

Reaction equation

HRID 1739155 reaction equation
N[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3]CSC.[CH3:10][O:11][C:12](=[O:34])[C@H:13]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N[C@H](C=O)[CH2:44][S:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)(C1C=CC=CC=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(OC(C)(C)C)=O>>[CH3:10][O:11][C:12](=[O:34])[C@H:13]([CH2:30][CH:31]([CH3:32])[CH3:33])[NH:14][C:15](=[O:29])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:3][C@H:2]([C:7]([O:9][C:31]([CH3:33])([CH3:32])[CH3:30])=[O:8])[CH2:44][S:45][C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)=[CH:18][C:17]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 6137L-MethionineHCID 10388929N-Boc-S-trityl-(L)-cysteinalHCID 10831027HCID 10831027, compound

Product 1

HCID 18392924HCID 18392924, compound

Procedure

This compound was prepared using the same method as for the preparation of methionine derivative (See Example 26, section B), using 4-amino-2-phenylbenzoyl-(S)-leucine methyl ester and N-Boc-S-trityl-(L)-cysteinal as starting materials. 1H NMR (CDCl3) δ 7.68 (d, 8.6 Hz, 1H), 7.33-7.41 (m, 11H), 7.17-7.29 (m, 9H), 6.50 (d, 8.6 Hz, 1H), 6.31 (s, 1H), 5.43 (d, 7.8 Hz, 1H), 4.60 (d, 6.1 Hz, 1H), 4.47 (ddd, 1H), 4.19 (br t, 1H), 3.77 (br m, 1H), 3.62 (s, 3H), 3.09 (t, 5.9 Hz, 2H), 2.45 (br m, 2H), 1.40 (s, 9H), 1.27-1.33 (m, 1H), 1.03-1.18 (m, 2H), 0.75 (dd, 6H); 13C (CDCl3) δ 173.2, 168.2, 155.6, 149.4, 144.4, 141.7, 141.2, 131.4, 129.5, 128.8, 128.5, 127.9, 127.6, 126.8, 122.7, 113.6, 111.3, 79.6, 67.1, 51.9, 50.9, 49.5, 47.1, 41.2, 34.3, 28.3, 24.4, 22.7, 21.8.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-fa2286157f454b4b95b0a25d2cdae653
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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