Sulfuric acid magnesium salt (1:1) → HCID 59524410, compound

HRID 2095050Notes

Reaction equation

HRID 2095050 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:18][C@@H:19]([CH2:24][OH:25])[C:20]([O:22][CH3:23])=[O:21].[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH:18][C@@H:19]([CH2:24][OH:25])[C:20]([O:22][CH3:23])=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 4311764Sodium borohydrideHCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Product 1

HCID 59524410HCID 59524410, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(tert-butyldimethylsilyloxy)benzaldehyde (Example 12-1c) 1.52 g (6.43 mmol), triethyl amine (5 mL) and (S)-methyl 2-amino-3-hydroxypropanoate hydrochloride (1.00 g, 6.43 mmol) in DCM (30 mL) was added MgSO4 and the solution was stirred at RT for 36 h. MgSO4 was then filtered off and DCM was removed under vacuum. The residue was dissolved in dry MeOH (40 mL), cooled to 0° C. and treated in small portions with NaBH4 (1.2 equiv.). The mixture was stirred at 0° C. for 3 h, quenched with water (10 mL) and concentrated by removing MeOH. The residue was extracted with Ethyl acetate to provide (S)-methyl 2-(3-(tert-butyldimethylsilyloxy)benzylamino)-3-hydroxypropanoate as yellowish oil (2.10 g, 96%). MS 340 (MH+).

Workup

  1. filtrationMgSO4 was then filtered off
  2. customDCM was removed under vacuum
  3. dissolutionThe residue was dissolved in dry MeOH (40 mL)
  4. temperaturecooled to 0° C.
  5. stirringThe mixture was stirred at 0° C. for 3 h
  6. customquenched with water (10 mL)
  7. concentrationconcentrated
  8. customby removing MeOH
  9. extractionThe residue was extracted with Ethyl acetate

Sources & evidence

ORD record
ord-26e5f84d3cb44021a2adad342be58ee2
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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