Sodium Iodide → Nalpha-Boc-Ndelta-Cbz-Ornithinyl 2-Benzothiazolyl Thioether

HRID 1067093Notes

Reaction equation

HRID 1067093 reaction equation
CS([O:5][CH2:6][C@H:7]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)=O.[I-].[Na+].[SH:32][C:33]1[S:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CN(C)C=O>[S:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[S:32][C:6](=[O:5])[C@H:7]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 15453141HCID 15453141, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 131722656Nalpha-Boc-Ndelta-Cbz-Ornithinyl 2-Benzothiazolyl ThioetherYield 41.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Nα-Boc-Nδ-Cbz-ornithinol methanesulfonate (100 mg), sodium iodide (70 mg), dimethylformamide (2.5 ml), 2-mercaptobenzothiazole (70 mg) and diisopropylethylamine (85 μl) was stirred at 70° C. for 12 h. After cooling to ambient temperature, the reaction mixture was poured into ethyl acetate and worked up. The crude material was chromatographed over silica gel (20 to 50 % ethyl acetate/hexane) to afford titled product (50 mg) as a white solid: 1H NMR (400 MHz, CDCl3) δ1.39 (s, 9H), 1.58-1.69 (m, 4H), 3.22 (m, 2H), 3.54 (m, 2H), 3.99 (m, 1H), 5.12 (s, 2H), 7.23-7.42 (m, 1H), 7.77 (d, J=10.3 Hz, 1H), and 7.86 (d, J=9.7 Hz, 1H).

Workup

  1. customThe crude material was chromatographed over silica gel (20 to 50 % ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c94fa640d67542dd81330f512d6468ba
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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