4-Methylmorpholine → HCID 131721363, compound

HRID 618146Notes

Reaction equation

HRID 618146 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[NH:22]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH2:23][C:24](O)=[O:25].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:8]([O:7][C:5](=[O:6])[C@@H:4]([NH:12][S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14])[CH2:3][NH:2][C:24](=[O:25])[CH2:23][NH:22][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Product 1

HCID 131721363HCID 131721363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amine 1-5 (0.42 g, 1.25 mmol), Cbz-Gly-OH (288 mg, 1.38 mmol), NMM (0.55 mL, 5.0 mmol) and BOP (829 mg, 1.88 mmol) were combined in 6 mL DMF. After stirring overnight the solvent was evaporated, the residue was taken up in EtOAc, the organic solution was washed with water (2×), 5% KHSO4, sat. NaHCO3 and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 60% EtOAc/hexane) provided 5-6 as a white glass.

Workup

  1. customwas evaporated
  2. washthe organic solution was washed with water (2×), 5% KHSO4, sat. NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcb22357eb9f41439e13b1e49edc6986
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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