Hydrochloric Acid → H-Gly-Leu-Ala-OBzl HCl

HRID 4984

Reaction equation

HRID 4984 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:15])=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].FC(F)(F)C(O)=O.N[C@H](C(N[C@H](C(OCC1C=CC=CC=1)=O)C)=O)CC(C)C.FC(F)(F)C([O-])=O.[ClH:68]>CCOCC.C(OCC)(=O)C>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH3:15])=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].[ClH:68]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 84468TrifluoroacetateHCID 16742166H-Leu-Ala-OBzlHCID 131717744Boc-Gly-Leu-Ala-OBzl

Product 1

HCID 131718105H-Gly-Leu-Ala-OBzl HCl

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparation of H-Leu-Ala-OBzl except that the trifluoroacetate salt was soluble in ether. The preparation was dissolved in ethyl acetate and treated with anhydrous hydrogen chloride. The resulting product was precipitated by the addition of ether to yield 7.7 g of H-Gly-Leu-Ala-OBzl HCl in a first crop.

Workup

  1. customThe resulting product was precipitated by the addition of ether

Sources & evidence

ORD record
ord-1e9e6ea312024abbb5827b12a87dd34a
Source dataset
uspto-grants-1993_09
Patent number
US05242904

Linked notes

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