Hydrochloric Acid → tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate

HRID 1374429Notes

Reaction equation

HRID 1374429 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:21][OH:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:32][O:33][CH2:34]Cl.Cl.[Cl-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:21][O:22][CH2:32][O:33][CH3:34])[CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[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 15043090(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 69350141tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoateYield 100.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate (14.26 g, 46.1 mmol) in dichloromethane (190 ml) were added under ice cooling 4-dimethylaminopyridine (0.28 g, 2.3 mmol), diisopropylethylamine (24 ml, 138 mmol) and chloromethyl methyl ether (105 ml, 138 mmol). The mixture was raised to room temperature. Twelve hours later, to the mixture were added ice water and 1N hydrochloric acid under cooling in an ice bath to adjust pH to about 3. To the mixture was added a saturated aqueous sodium chloride solution and the solution was separated with a separating funnel. The organic layer was washed once with water and twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate (16.4 g, 100%).

Workup

  1. temperatureunder cooling in an ice bath
  2. customthe solution was separated with a separating funnel
  3. washThe organic layer was washed once with water and twice with a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-292db17d97d94900a2f96eb40c7355fc
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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