Trifluoroacetic acid → N-(Toluene-4-sulfonyl)-L-prolyl-L-asparagine

HRID 2230018Notes

Reaction equation

HRID 2230018 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:25][C:26](=[O:33])[C@H:27]([CH2:29][C:30](=[O:32])[NH2:31])[NH2:28])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[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:28][C@H:27]([C:26]([OH:33])=[O:25])[CH2:29][C:30](=[O:32])[NH2:31])=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 16218498tert-Butyl L-asparaginate--hydrogen chloride (1/1)HCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 9951963N-(Toluene-4-sulfonyl)-L-prolyl-L-asparagine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(Toluene4-sulfonyl)-L-proline hydrate was coupled to L-asparagine tert-butyl ester hydrochloride using the procedure described in Method 3. The title compound was prepared, via cleavage of the tert-butyl ester using trifluoroacetic acid in CH2Cl2, to provide a solid, mp=178-180° C.

Workup

  1. customto provide a solid, mp=178-180° C.

Sources & evidence

ORD record
ord-75c22a6a627e494d820b465320793dc8
Source dataset
uspto-grants-2002_07
Patent number
US06423688B1

Reaction notes

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