4-Methylmorpholine → HCID 178512912, compound

HRID 1079051Notes

Reaction equation

HRID 1079051 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][CH2:21][CH2:22][N:23]=[C:24]([NH:26][N+]([O-])=O)[NH2:25])=[O:17])[C:8]3[C:13]([C:4]2=[CH:3][CH:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[NH:18]([C:16]([O:15][CH2:14][CH:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:17])[C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12096824Fmoc-Arg(NO2)-OH

Product 1

HCID 178512912HCID 178512912, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-fluorenylmethyloxycarbonyl-Ng -nitro-L-arginine (from step 2, 26.8 mmol), BOP (30 mmol), HOBt (30 mmol) and NMM (55 mmol) in 40 mL of DMF was mixed with 10 g of PAC resin (α-methylphenacyl linker attached to polystyrene-1% divinylbenzene, substitution 0.97mmol/g, supplied by Bachem Bioscience, Philadelphia, Pa.) and stirred for 4 h. The resin was filtered off, washed with DMF, DCM and MeOH and dried to yield the final product Fmoc-Arg (NO2 )-Resin (11.1 g). The resin, Fmoc-Arg (NO2 )-Resin (11.1 g) was treated with 100 ml of a solution containing piperidine (30%), DMF (35%) and toluene (35%) and stirred for 2.5 hrs. The Fmoc removed resin was filtered and consecutively washed with DCM/DMF (50:50) and MeOH to yield the title product (9.2 g).

Workup

  1. filtrationThe resin was filtered off
  2. washwashed with DMF, DCM and MeOH
  3. customdried

Sources & evidence

ORD record
ord-4891268b478a4fcfa66b97550f58403b
Source dataset
uspto-grants-1996_08
Patent number
US05550262

Reaction notes

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