Hydrochloric Acid → n-(Benzyloxycarbonyl)-4-amino-3-methyl-l-phenylalanine methyl ester hydrochloride salt

HRID 844873Notes

Reaction equation

HRID 844873 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23]C(OC(C)(C)C)=O)=[C:19]([CH3:31])[CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[ClH:33]>O1CCOCC1.C(OCC)C>[ClH:33].[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([CH3:31])[CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69336452N-(benzyloxycarbonyl)-4-[(1,1-dimethylethoxy)carbonyl]amino-3-methyl-L-phenylalanine methyl ester

Product 1

HCID 69336581n-(Benzyloxycarbonyl)-4-amino-3-methyl-l-phenylalanine methyl ester hydrochloride saltYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-(benzyloxycarbonyl)-4-[(1,1-dimethylethoxy)carbonyl]amino-3-methyl-L-phenylalanine methyl ester (4.52 mmol, 2 g) in dioxane (12 mL) was added 4N hydrochloric acid in dioxane (48 mmol, 2 mL) at room temperature and the solution was stirred for approximately 2 h as a white precipitate was formed. The solids were diluted with diethyl ether, the mother liquor was decanted and the residue was dried first on a rotary evaporator and then under high vacuum to afford 1.487 g (87% yield) of N-(benzyloxycarbonyl)-4-amino-3-methyl-L-phenylalanine methyl ester hydrochloride salt as an amorphous yellow solid. FAB-HRMS m/e calcd for C19H22N2O4 (M+H) 343.0142, found 343.0144.

Workup

  1. customwas formed
  2. customthe mother liquor was decanted
  3. customthe residue was dried first on a rotary evaporator

Sources & evidence

ORD record
ord-007392d577c94da39bbe04a572621e64
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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