Hydrochloric Acid → HCID 71777655, compound

HRID 236465Notes

Reaction equation

HRID 236465 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=[O:4].[NH2:13][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH3:15].[ClH:20].Cl>O1CCOCC1>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:13][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH3:15])=[O:5].[NH2:1][CH2:2][C:3]([NH:13][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH3:15])=[O:4].[ClH:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733257Alanine methyl ester hydrochloride

Product 2

HCID 11821341HCID 11821341, compoundHCID 71777655HCID 71777655, compoundYield 137.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Boc-Gly-Ala-OCH3 was prepared by coupling Boc-Gly-OH (35.0 g, 200 mmol) to H-Ala-OCH3.HCl (27.9 g, 200 mmol) using a mixed anhydride procedure. The resulting product (43.5 g, 167 mmol) was deblocked with anhydrous HCl in dioxane. After deblocking, crystallization from dioxane:ether yielded 27.1 g of H-Gly-Ala-OCH3.HCl.

Workup

  1. customcrystallization from dioxane

Sources & evidence

ORD record
ord-10ffd0f80fdf4789b85527ce85f81d3e
Source dataset
uspto-grants-1987_02
Patent number
US04644055

Reaction notes

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