4-Methylmorpholine → Boc-Val-Pro-OBzl

HRID 2087122Notes

Reaction equation

HRID 2087122 reaction equation
[NH:1]1[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:17]([C:21](O)=[O:22])[CH:18]([CH3:20])[CH3:19].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)(Cl)Cl>[NH:16]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C@H:17]([C:21]([N:1]1[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4])=[O:22])[CH:18]([CH3:19])[CH3:20]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 736155Benzyl L-prolinate

Product 1

HCID 14304307Boc-Val-Pro-OBzl

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Boc-Val-Pro-OBzl was prepared by dissolving H-Pro-OBzl (20 g, 83 mmol) in 50 mL of chloroform and adding Boc-Val-OH (18.0 g, 83 mmol), HOBt (23.0 g, 165 mmol), NMM (9.0 mL, 83 mmol) and DCC (17.0 g, 83 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was filtered and solvent was evaporated. Ethyl acetate was added and insoluble material was removed by filtration. The filtrate was washed with 0.2N HCl, 5% NaHCO3, and saturated aqueous NaCl. It was dried over Na2SO4, filtered and evaporate to give a white solid (30 g, 75 mmol, 90%). ESI/MS calculated for C22H32N2O5+H: 405.2. Found 405.6.

Workup

  1. filtrationThe mixture was filtered
  2. customsolvent was evaporated
  3. additionEthyl acetate was added
  4. custominsoluble material was removed by filtration
  5. washThe filtrate was washed with 0.2N HCl, 5% NaHCO3, and saturated aqueous NaCl
  6. dry with materialIt was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporate

Sources & evidence

ORD record
ord-2be8bbed53e74f28bed492e4e090b7e6
Source dataset
uspto-grants-2004_04
Patent number
US06727366B2

Reaction notes

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