Ethanol → L-Valine, N-[[(4-nitrophenyl)methoxy]carbonyl]-

HRID 54816Notes

Reaction equation

HRID 54816 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:23])OC2C=CC([N+]([O-])=O)=CC=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27].C(N(CC)CC)C.C(O)C>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][O:11][C:12]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 6287L-ValineHCID 8471TriethylamineHCID 21829967Carbonic acid 4-Nitrophenyl (4-Nitrophenyl)methyl Ester

Product 1

HCID 54494215L-Valine, N-[[(4-nitrophenyl)methoxy]carbonyl]-Yield 35.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared by the procedure of Example 255 using 14.73 g of product from Example 254, 5.42 g of L-valine, 12.75 ml of triethylamine and 556 ml of 4:1 ethyl alcohol:water to give 4.89 g of the desired product after chromatography.

Sources & evidence

ORD record
ord-25689f53ecad44ddbac2e2808a05892a
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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