Lithium Hydroxide → N-(Toluene-4sulfonyl)-L-prolyl-beta-(2-naphthyl)-L-alanine

HRID 279706Notes

Reaction equation

HRID 279706 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:37])[C@H:24]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)[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:37])=[O:22])[CH2:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 56777259methyl (2S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochlorideHCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 18714224N-(Toluene-4sulfonyl)-L-prolyl-beta-(2-naphthyl)-L-alanine

Reagents, catalysts & solvents 1

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

Procedure

N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to β-(2-naphthyl)-L-alanine 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-e969b53c132d433f8b3b70b2a601bda0
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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