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

HRID 2230023Notes

Reaction equation

HRID 2230023 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:33])[C@H:24]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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:33])=[O:22])[CH2:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 22861687methyl (2S)-2-amino-3-cyclohexylpropanoate hydrochlorideHCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 22096124N-(Toluene-4-sulfonyl)-L-prolyl-beta-cyclohexyl-L-alanine

Reagents, catalysts & solvents 1

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

Procedure

N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to β-cyclohexylalanine 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-69c44519afea47a98f9d8aad894f376a
Source dataset
uspto-grants-2002_07
Patent number
US06423688B1

Reaction notes

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