4-Methylmorpholine → HCID 23591746, compound

HRID 430904Notes

Reaction equation

HRID 430904 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:25](=[O:26])[CH2:24][NH:23][C:21]([O:20][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:22])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 23591746HCID 23591746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 3 grams of (3-Amino-propyl)-carbamic acid tert-butyl ester in 15 ml of dimethylformamide was added 3 grams of N-benzyloxycarbonyl glycine, 4.7 mL of N-methylmorpholine and 5.06 grams of TBTU. The reaction was cooled to 0 degrees C. for 30 minutes then allowed to stir at room temperature overnight. The volatiles were removed under reduced pressure and the resulting material was dissolved in ethyl acetate and washed with 10% citric acid. The aqueous was extracted an additional two times with ethyl acetate, combined and washed with water, saturated aqueous sodium bicarbonate, water, brine and dried over MgSO4. The volatiles were removed under reduced pressure and the resulting material was crystallized from EtOAc/hexane affording 4.55 grams of the desired product as a tan solid. LRMS found 388.3=(M+Na)+

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe resulting material was dissolved in ethyl acetate
  3. washwashed with 10% citric acid
  4. extractionThe aqueous was extracted an additional two times with ethyl acetate
  5. washwashed with water, saturated aqueous sodium bicarbonate, water, brine
  6. dry with materialdried over MgSO4
  7. customThe volatiles were removed under reduced pressure
  8. customthe resulting material was crystallized from EtOAc/hexane affording 4.55 grams of the desired product as a tan solid

Sources & evidence

ORD record
ord-6f5a728a5eb547139099906c2a352b62
Source dataset
uspto-grants-2003_12
Patent number
US06656448B1

Reaction notes

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