H-Gln-OtBu hydrochloride → N-(Toluene-4-sulfonyl)-L-prolyl-L-glutamine

HRID 2230020Notes

Reaction equation

HRID 2230020 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:34])[C@H:27]([CH2:29][CH2:30][C:31](=[O:33])[NH2:32])[NH2:28])(C)(C)C>>[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:34])=[O:25])[CH2:29][CH2:30][C:31](=[O:33])[NH2:32])=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 15602445H-Gln-OtBu hydrochlorideHCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 53697337N-(Toluene-4-sulfonyl)-L-prolyl-L-glutamine

Procedure

N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to L-glutamine tert-butyl ester hydrochloride using the procedure described in Method 3. The title compound, prepared via cleavage of the tert-butyl ester using trifluoroacetic acid in CH2Cl2, was recovered as a solid, mp=45-55° C.

Sources & evidence

ORD record
ord-2e285f391a1643879aa6911cf3c6871a
Source dataset
uspto-grants-2002_07
Patent number
US06423688B1

Reaction notes

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