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

HRID 263497Notes

Reaction equation

HRID 263497 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) in THF (500 mL) and N-methylmorpholine (13.1 g, 120 mmol), isobutylchloroformate (15.6 mL, 1.2 mmol) was added dropwise. The reaction mixture was stirred for a few minutes and 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, the reaction mixture was filtered 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), 10% aqueous NaHCO3 (1×400 mL), water (1×400 mL) and saturated salt solution (1×300 mL). The solution was dried (anhydrous K2CO3), filtered and concentrated to yield the titled compound (53 g).

Workup

  1. stirringstirred for 18 h
  2. customUpon completion of the reaction
  3. filtrationthe reaction mixture was filtered
  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), 10% aqueous NaHCO3 (1×400 mL), water (1×400 mL) and saturated salt solution (1×300 mL)
  7. dry with materialThe solution was dried (anhydrous K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-926680f640c445d68e90af716e3fe069
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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