4-Methylmorpholine → HCID 131718970, compound

HRID 1654587Notes

Reaction equation

HRID 1654587 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=O)[C:3]([CH3:6])([CH3:5])[CH3:4].[NH2:20][C@H:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24].Cl.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([NH:20][C@H:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:9])[C:3]([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9899995(2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acidHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 131718970HCID 131718970, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Z-Tle (15.6 g, 59.1 mmol), Leu-OEt HCl (11.56 g, 59.1 mmol), and N-methyl morpholine (NMM) (12.75 mL) are mixed with 45 mL of DMF and a cloudy suspension forms. The mixture is cooled to 0° C. and treated with TBTU (19.1 g, 59.48 mmol), then stirred at 0° C. for 15 minutes, then removed from the cold bath and stirred for 1.5 hours. The mixture is poured into 500 mL of a saturated solution of sodium carbonate which is then extracted with two 350 mL portions of ethyl acetate. The combined organic extracts are washed with 500 mL of 1 M KHSO4 water and brine and then dried over sodium sulfate. The solvents are removed to give Z-Tle-Leu-OEt (24.1 g). FABMS M+1 407

Workup

  1. customremoved from the cold bath
  2. stirringstirred for 1.5 hours
  3. additionThe mixture is poured into 500 mL of a saturated solution of sodium carbonate which
  4. extractionis then extracted with two 350 mL portions of ethyl acetate
  5. washThe combined organic extracts are washed with 500 mL of 1 M KHSO4 water and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvents are removed

Sources & evidence

ORD record
ord-a62e2435ec1348bbb0eec7feef7a588f
Source dataset
uspto-grants-1995_04
Patent number
US05407916

Reaction notes

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