4-Methylmorpholine → HCID 54449090, compound

HRID 1654592Notes

Reaction equation

HRID 1654592 reaction equation
[C:1]1(=[O:32])[N:5]([CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[C:10]([OH:12])=O)[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.Cl.[C:34]([O:38][C:39](=[O:45])[C@@H:40]1[CH2:44][CH2:43][CH2:42][NH:41]1)([CH3:37])([CH3:36])[CH3:35].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:34]([O:38][C:39](=[O:45])[C@@H:40]1[CH2:44][CH2:43][CH2:42][N:41]1[C:10](=[O:12])[CH:9]([CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]2[C:1]1=[O:32])[CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[O:26])[C:18]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]2[C:20]1=[O:21])([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6453107tert-Butyl L-prolinate hydrochlorideHCID 20077933HCID 20077933, compound

Product 1

HCID 54449090HCID 54449090, compoundYield 245%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bis(3-phthalimidopropyl)acetic acid (Step B) (2.5 g, 5.5 mmol), proline tert-butyl ester hydrochloride (0.42 g, 2.0 mmol), and N-methylmorpholine (1.19 g, 5.4 mmol) in 7 mL of DMF are cooled to 0° C. and treated with TBTU (0.64 g, 2.0 mmol). The mixture is then stirred at room temperature for 18 hours. The reaction mixture is poured into 70 mL of saturated sodium bicarbonate solution and extracted with two 50 mL portions of ethyl acetate. The combined organics are washed with 1 M KHSO4, saturated aqueous bicarbonate and brine, and dried over Na2SO4. The volatiles are removed under reduced pressure and the residue is chromatographed over silica gel (4:1 chloroform, ethyl acetate eluent) to give 2.88 g of 1-[Bis(3-phthalimidopropyl)acetyl]-proline tert-butyl ester.

Workup

  1. extractionextracted with two 50 mL portions of ethyl acetate
  2. washThe combined organics are washed with 1 M KHSO4, saturated aqueous bicarbonate and brine
  3. dry with materialdried over Na2SO4
  4. customThe volatiles are removed under reduced pressure
  5. customthe residue is chromatographed over silica gel (4:1 chloroform, ethyl acetate eluent)

Sources & evidence

ORD record
ord-cd4bef6bc6544c21b0fe4bf427bb7cad
Source dataset
uspto-grants-1995_04
Patent number
US05407916

Reaction notes

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