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

HRID 1770602Notes

Reaction equation

HRID 1770602 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 disolved 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. temperaturecooled to 0° C.
  4. stirringThe mixture was stirred at 0° C. for 3 h
  5. customquenched with water (10 mL)
  6. concentrationconcentrated
  7. customby removing MeOH
  8. extractionThe residue was extracted with Ethyl acetate

Sources & evidence

ORD record
ord-1d506ae9837840629c470bef95c6e449
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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