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

HRID 2081969Notes

Reaction equation

HRID 2081969 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.Cl>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]

Participants

8

Reactant 5

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

Product 1

HCID 131717745H-Gly-Leu-Ala-OBzl

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-1d9afa66be7e41448fb046f228131e5d
Source dataset
uspto-grants-1993_02
Patent number
US05187157

Reaction notes

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