4-Methylmorpholine → HCID 86749876, compound

HRID 863789Notes

Reaction equation

HRID 863789 reaction equation
C([C@@:5]([C:22]([O-:24])=[O:23])([CH2:17][CH2:18][C:19]([O-:21])=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(C)(C)C.C[N:26]1[CH2:31][CH2:30][O:29]C[CH2:27]1.ClC(O[CH2:36][CH:37]([CH3:39])[CH3:38])=O.[C:40](N(C)CC(O)=O)([CH3:43])([CH3:42])[CH3:41].[O:50]1CCCC1>>[C:37]([C:31]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:30]([OH:29])=[O:50])[N:26]([C:19](=[O:21])[CH2:18][CH2:17][C@@H:5]([C:22]([OH:24])=[O:23])[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH3:27])([CH3:39])([CH3:38])[CH3:36]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 8028Tetrahydrofuran2×HCID 62365Isobutyl chloroformateHCID 21902549HCID 21902549, compoundHCID 86749877HCID 86749877, compound

Product 1

HCID 86749876HCID 86749876, compound

Procedure

To a stirred solution of α-tert-butyl-N-BENZYLOXYCARBONYL-L-GLUTAMATE (1.63 g) and N-methylmorpholine (0.487 g) in dry tetrahydrofuran (8 ml) cooled to -20° C. was added isobutyl chloroformate (0.657 g). After 10 minutes a solution of tert-butyl-N-methylglycine (0.70 g) in tetrahydrofuran (8 ml) was added. Stirring was continued for 10 minutes at -20° C., and then at laboratory temperature for 4 hours. N-methylmorpholine hydrochloride was filtered off and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using 5% ethyl acetate in dichloromethane as eluant, affording di-tert-butyl-N-methyl-[N-(benzyloxycarbonyl)-L-γ-glutamyl]glycine as a yellow oil (1.73 g).

Workup

  1. waitat laboratory temperature for 4 hours
  2. filtrationN-methylmorpholine hydrochloride was filtered off
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-cedcc862f2e44cb68d719fe7fb92675e
Source dataset
uspto-grants-1996_10
Patent number
US05561133

Reaction notes

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