Lithium Hydroxide → N-(Toluene-4-sulfonyl)-L-prolyl-Nepsilon-(carbobenzyloxy)-L-lysine

HRID 1182038Notes

Reaction equation

HRID 1182038 reaction equation
O.[C:2]1([CH3:19])[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:18][CH2:17][CH2:16][C@H:12]2[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.C[O:22][C:23](=[O:41])[C@H:24]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[NH2:25].[Li+].[OH-]>C1COCC1.O>[C:2]1([CH3:19])[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:18][CH2:17][CH2:16][C@H:12]2[C:13]([NH:25][C@H:24]([C:23]([OH:41])=[O:22])[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 1293537127894-50-4HCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 53968365N-(Toluene-4-sulfonyl)-L-prolyl-Nepsilon-(carbobenzyloxy)-L-lysine

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to Nε-Cbz-L-lysine methyl ester hydrochloride using the procedure described in Method 3. The title compound was prepared via hydrolysis of the methyl ester using LiOH in THF/water.

Sources & evidence

ORD record
ord-2e3d2dbb471343069139593e528e2bd8
Source dataset
uspto-grants-2007_10
Patent number
US07288526B2

Reaction notes

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