Sodium Iodide → HCID 23519193, compound

HRID 1836605Notes

Reaction equation

HRID 1836605 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:11]([NH:18][C@H:19]([C:29]([OH:31])=[O:30])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[O:8]1[CH2:9][CH2:10][N:5]([C:3]([CH2:2][O:31][C:29](=[O:30])[C@H:19]([CH2:20][O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:18][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[O:4])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 23519193HCID 23519193, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

O-Benzyl-L-serine (10.0 g, 51.3 mmol), di-tert-butyl-dicarbonate (11.2 g, 51.4 mmol) and 1 N sodium hydroxide (103 mL, 103 mmol) are stirred together in 100 mL of dioxane at room temperature for 16 hours. The mixture is concentrated in vacuo, taken up in water, acidified to pH 1 with 6 N HCl and extracted with ethyl acetate. The organic layer is washed with water, then brine, and dried over anhydrous magnesium sulfate. The mixture is filtered and concentrated in vacuo to give BOC-O-benzyl-L-serine as an oil. 4-(2-Chloroacetyl)morpholine (1.22 g, 7.48 mmol) is added to a solution of BOC-O-benzyl-L-serine (2.20 g, 7.46 mmol), triethylamine (0.75 g, 7.43 mmol) and sodium iodide (0.11 g, 0.73 mmol) in 5 mL of N,N-dimethylformamide and the mixture stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate, washed with water, then with brine, and dried over anhydrous magnesium sulfate. The mixture is filtered and concentrated in vacuo to give a yellow oil. The oil is chromatographed on silica gel with hexane:ethyl acetate:methanol (35:60:5) to give BOC-O-benzyl-L-serine morpholinocarbonylmethyl ester as a colorless oil. HCl gas is bubbled through a solution of the carbamate ester (1.72 g, 4.08 mmol) in methylene chloride (50 mL) for 5 minutes and the mixture is stirred at room temperature for 3 hours. The resulting mixture is concentrated in vacuo to yield O-benzyl-L-serine morpholinocarbonylmethyl ester as a foam.

Workup

  1. washwashed with water
  2. dry with materialwith brine, and dried over anhydrous magnesium sulfate
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customThe oil is chromatographed on silica gel with hexane:ethyl acetate:methanol (35:60:5)

Sources & evidence

ORD record
ord-0b4df7c440554b4ab8f272449fc6cf03
Source dataset
uspto-grants-2004_08
Patent number
US06777443B2

Reaction notes

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