4-Methylmorpholine → Boc-Asp(O-cHex) Man(4-MBzl)

HRID 263501Notes

Reaction equation

HRID 263501 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CN1CCOCC1.[OH:30][CH:31]1[O:47][C@H:46]([CH2:48][OH:49])[C@@H:36]([O:37][CH2:38][C:39]2[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=2)[C@H:34]([OH:35])[C@@H:32]1[OH:33]>C1COCC1.C(OC(Cl)=O)C(C)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4](=[O:12])[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH:30][CH:31]1[O:47][C@H:46]([CH2:48][OH:49])[C@@H:36]([O:37][CH2:38][C:39]2[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=2)[C@H:34]([OH:35])[C@@H:32]1[OH:33]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 7009416Boc-Asp(OcHx)-OHHCID 131720063Man(4-MBzl)

Product 1

HCID 131720065Boc-Asp(O-cHex) Man(4-MBzl)Yield 92.1%

Reagents, catalysts & solvents 2

HCID 62365Isobutyl chloroformateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold solution of Boc-Asp(O-cHex) (31.5 g, 100 mmol) and N-methylmorpholine (13.1 g, 120 mmol) in THF (500 mL), isobutylchloroformate (15.6 mL, 1.2 mmol) was added dropwise. The reaction mixture was stirred for a few minutes, then a solution of Man(4-MBzl) (22.0 g, 96 mmol) in THF (500 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. Upon completion of the reaction (monitored by TLC), the amine sand the filtered off and the filtrate was concentrated to dryness. The residue was dissolved in ethyl acetate (500 mL) and washed successively with 5% aqueous citric acid (3×150 mL), water (1×400 mL), aqueous NaHCO3 (1×300 mL), water (1×400 mL) and saturated salt solution (1×30 mL). The organic solvent was dried (anhydrous K2CO3), filtered and concentrated to yield the title product (53 g).

Workup

  1. stirringstirred for 18 h
  2. customUpon completion of the reaction (monitored by TLC)
  3. filtrationthe amine sand the filtered off
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  6. washwashed successively with 5% aqueous citric acid (3×150 mL), water (1×400 mL), aqueous NaHCO3 (1×300 mL), water (1×400 mL) and saturated salt solution (1×30 mL)
  7. dry with materialThe organic solvent was dried (anhydrous K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8f1bfa25f2a246b5b287515bfd29d179
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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