Diisopropylethylamine → HCID 67094887, compound

HRID 2112085Notes

Reaction equation

HRID 2112085 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=O.Cl.[CH3:15][O:16][C:17](=[O:27])[CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19].C(N(C(C)C)C(C)C)C.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([NH:19][CH:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([O:16][CH3:15])=[O:27])=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 957952-Amino-6-nitro-benzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3084017Methyl 3-phenyl-DL-alaninate hydrochloride

Product 1

HCID 67094887HCID 67094887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.18 g (6.5 mmol) 2-amino-6-nitrobenzoic acid, 1.0 g (4.6 mmol) D,L-phenylalanine-methylester hydrochloride, 4.05 ml (23.2 mmol) N-ethyldiisopropylamine are combined with 2.5 ml of tetrahydrofuran. 1.71 g (5.1 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate are added to this reaction mixture and it is heated for 12 h to 50° C. Then the solvent is eliminated in vacuo and the crude product is purified by chromatography. The carrier used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (50:50).

Workup

  1. temperatureis heated for 12 h to 50° C
  2. customthe crude product is purified by chromatography
  3. additiona mixture of cyclohexane:ethyl acetate (50:50)

Sources & evidence

ORD record
ord-f7a43c7a3a8145f08ac9e0742683b791
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

Loading…