Vanillin → N-benzyloxycarbony-D-valine isopropylamide

HRID 330122

Reaction equation

HRID 330122 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20].O=CC1C=CC(O)=C(OC)C=1>C(OCC)(=O)C.CCCCCC>[CH:19]([NH:22][C:16](=[O:18])[C@@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1183VanillinHCID 6363IsopropylamineHCID 712434N-alpha-Benzyloxycarbonyl-D-valine

Product 1

HCID 14723623N-benzyloxycarbony-D-valine isopropylamide

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Reaction of N-benzyloxycarbonyl-D-valine with isopropylamine by the method of Example 20, Part A afforded a quantitative yield of N-benzyloxycarbonyl-D-valine isopropylamide of R 0.61 (TLC, ethyl acetate/hexane, 1:1, vanillin spray).

Sources & evidence

ORD record
ord-4c3e69659dee44c18274040f6b2db3d0
Source dataset
uspto-grants-1990_01
Patent number
US04894464

Linked notes

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