Hydrochloric Acid → HCID 137231655, compound

HRID 52598Notes

Reaction equation

HRID 52598 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:20]([OH:22])=O)[CH2:10][CH2:11][CH2:12][N:13]=[C:14]([NH:16][N+:17]([O-:19])=[O:18])[NH2:15])=[O:7])([CH3:4])[CH3:3].Cl.[CH2:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[CH:29][CH:28]=1)[CH3:25].C(OC1C=CC(C#N)=CC=1)C.Cl.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(O)[C@H](O)[C@H]1OC(=O)C(O)=C1O>[Pd].C(Cl)Cl.C(N(CC)CC)C>[NH2:15][C:14](=[N:16][N+:17]([O-:19])=[O:18])[NH:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:20]([NH:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:24][CH3:25])=[CH:28][CH:29]=1)=[O:22])[NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1411764-Ethoxybenzoic acid nitrileHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7021876Boc-D-Arg(NO2)-OHHCID 18975845HCID 18975845, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 137231655HCID 137231655, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Prepared analogously to Example 8a) from Boc-D-Arg-(NO2)-OH, 4-ethoxybenzenemethylamine-hydrochloride (mp.: 262°-264° C.; from 4-ethoxybenzonitrile by catalytic hydrogenation in the presence of palladium/animal charcoal and aqueous hydrochloric acid), triethylamine and TBTU in a yield of 77% of theory. IR (CH2Cl2): 1730 cm-1 (ester-C=O) 1675 cm-1 (amide C=O) 1510 cm-1 (amide II)

Sources & evidence

ORD record
ord-e7044d2e21e443a88af663f3fb94999d
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Reaction notes

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