Hydrochloric Acid → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

HRID 900158Notes

Reaction equation

HRID 900158 reaction equation
[CH3:1][C@H:2]([NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:3]([OH:5])=[O:4].ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.CNC.[O:27]1[CH2:31]C[CH2:29][CH2:28]1.Cl.[O:33]1CCOC[CH2:34]1.C[N:40]([CH3:43])[CH:41]=[O:42]>O>[CH3:19][CH:18]([C@H:43]([NH:40][C:41]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:42])[C:31]([OH:27])=[O:33])[CH3:23].[CH3:28][CH2:29][C@@H:1]([C@H:2]([NH:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[C:3]([OH:5])=[O:4])[CH3:34].[CH3:13][C:10]([O:9][C:7]([NH:6][C@H:2]([C:3]([OH:5])=[O:4])[CH2:1][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:8])([CH3:12])[CH3:11]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanine

Product 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 83693Boc-L-ValineHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-t-BOC-L-alanine 100-a (1.89 g, 9.99 mmol) and 1-hydroxybenzotriazole (270 mg, 2.00 mmol) in dimethylformamide (20 ml), a solution of dimethyl amine in 2.0 M tetrahydrofuran (7.50 ml, 15.0 mmol) and 1-ethyl-3-(3-dimethyl aminopropyl)-carbodiimide hydrochloride (2.30 g, 12.0 mmol) was added at room temperature and stirred for 4 hours. The mixture was mixed with water (50 ml) and extracted with ethyl acetate (100 ml). The extract was washed with water (20 ml) twice and brine (20 ml), and dried over sodium sulfate anhydrous. The residue, which was obtained from the mixture by evaporation in vacuo, was mixed with a solution of hydrogen chloride in 4M dioxane (25 ml, 100 mmol) and stirred for 45 min. The solvent was evaporated in vacuo to give a crude Compound 101-a, which was allowed to react without purification. In a manner similar to above, N-t-BOC-L-valine, N-t-BOC-L-leucine, N-t-BOC-L-isoleucine, N-t-BOC-L-phenylalanine and N□-t-BOC-Nlm-(benzyloxymethyl)-L-histidine each gave crude Compounds, 101-b to 101-f, respectively.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe extract was washed with water (20 ml) twice
  3. dry with materialbrine (20 ml), and dried over sodium sulfate anhydrous
  4. customThe residue, which was obtained from the mixture by evaporation in vacuo
  5. stirringstirred for 45 min
  6. customThe solvent was evaporated in vacuo
  7. customto give a crude Compound 101-a, which
  8. customto react without purification

Sources & evidence

ORD record
ord-c84069c7cf4446b89b36d0e45f8dde5e
Source dataset
uspto-grants-2008_04
Patent number
US07358249B2

Reaction notes

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