Fmoc-val-osu → Fmoc-Val-Lys(Mtr)

HRID 1883296Notes

Reaction equation

[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@H:2]([C:6](ON1C(=O)CCC1=O)=[O:7])[CH:3]([CH3:5])[CH3:4].[NH2:33][C@H:34]([C:54]([OH:56])=[O:55])[CH2:35][CH2:36][CH2:37][CH2:38][NH:39][S:40]([C:43]1[C:52]([CH3:53])=[C:50]([CH3:51])[C:47]([O:48][CH3:49])=[CH:46][C:44]=1[CH3:45])(=[O:42])=[O:41]>>[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:17])[C@H:2]([C:6]([NH:33][C@H:34]([C:54]([OH:56])=[O:55])[CH2:35][CH2:36][CH2:37][CH2:38][NH:39][S:40]([C:43]1[C:52]([CH3:53])=[C:50]([CH3:51])[C:47]([O:48][CH3:49])=[CH:46][C:44]=1[CH3:45])(=[O:42])=[O:41])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

Reactant 2

HCID 11339559Fmoc-val-osu

HCID 15662507Lys(Mtr)

Product 1

HCID 131724482Fmoc-Val-Lys(Mtr)

Procedure

This was prepared from Fmoc-Val-OSu 7b (20.7 mmol) and Lys(Mtr) 2 (9.09 g, 1.05 equiv) as described above for 8a (15.28 g, 100%). 1H-NMR (CDCl3/CD3OD) δ 0.85 (m, 6H), 1.20 (m, 2H), 1.59 (m, 4H), 1.99 (m, 1H), 2.41 (m, 2H), 3.71 (s, 3H), 4.21 (m, 5H), 6.78 (d, 2H), 7.29 (m, 16H), 7.51 (brt, 2H), 7.71 (d, 2H). MS (FAB) 740 (MH)+, 762 (M+Na)+. HRMS Calcd: 740.3700. Found: 740.3712.

Sources & evidence

ORD record: ord-efc5d37b54d846689ae4d5ec96198fd6
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759509B1

Reaction notes

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