Lithium Hydroxide → HCID 54006895, compound

HRID 1370232Notes

Reaction equation

HRID 1370232 reaction equation
[OH2:1].[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.[Li+].[OH-:21].F[C:23](F)(F)[C:24]([OH:26])=[O:25]>C1COCC1.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:11][C@H:12]([C:16]([OH:21])=[O:1])[CH2:13][CH2:23][C:24]([OH:26])=[O:25])=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 69463844N-tosyl-(s)-proline monohydrate

Product 1

HCID 54006895HCID 54006895, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

N-(Toluene-4-sulfonyl)-L-proline hydrate was coupled to L-5-(1,1-dimethylethyl)-glutamic acid methyl ester hydrochloride using the procedure described in Method 3. The methyl ester was hydrolyzed using LiOH in THF/water to provide a solid, mp=164-166° C. The title compound was prepared, via cleavage of the t-butyl ester using trifluoroacetic acid in CH2Cl2, as a solid, mp=>200° C.

Workup

  1. customto provide a solid, mp=164-166° C

Sources & evidence

ORD record
ord-1002b7faaa594d98bbf244b0ef7bf809
Source dataset
uspto-grants-2003_06
Patent number
US06583139B1

Reaction notes

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