Hydrochloric Acid → HCID 11003094, compound

HRID 1374408Notes

Reaction equation

HRID 1374408 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:22][OH:23])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:33][O:34][CH2:35]Cl.Cl.[Cl-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:22][O:23][CH2:33][O:34][CH3:35])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 86592518HCID 86592518, compound

Product 1

HCID 11003094HCID 11003094, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate (15.05 g, 46.5 mmol) in dichloromethane (150 ml) were added under the ice cooling 4-dimethylaminopyridine (120 mg, 1 mmol), diisopropylethylamine (26 ml, 150 mmol) and chloromethyl methyl ether (12 ml, 150 mmol), and the mixture was raised to the room temperature. Ten hours later the mixture was adjusted to pH about 3 with ice water and 1N hydrochloric acid under cooling in an ice bath. After adding a saturated aqueous sodium chloride solution and separating the mixture with a separating funnel, the organic layer was washed once with water and twice with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and the organic solvent was removed under reduced pressure to give tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}-5-(methoxymethoxy)pentanoate (16.87 g, 99%).

Workup

  1. customTen hours
  2. temperatureunder cooling in an ice bath
  3. customseparating the mixture with a separating funnel
  4. washthe organic layer was washed once with water and twice with a saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-35bace9723db48f2a0542b3a26c739eb
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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