Hydrochloric Acid → (2R)-3-hydroxy-2-(tetradecanoylamino)propanoic acid

HRID 1196065

Reaction equation

HRID 1196065 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(N(CC)CC)C.[C:15]([O-])(=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].S([O-])(OC(C)(C)S(OC1C=CC(O)=CC=1)(=O)=O)(=O)=O.Cl>O>[C:15]([NH:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])(=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 71077D-SerineHCID 4075158MyristateHCID 867457864-Hydroxyphenyldimethylsulfomethyl sulfate

Product 1

HCID 54198556(2R)-3-hydroxy-2-(tetradecanoylamino)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

D-serine 2.0 g (0.02 mol) and triethylamine 2.8 ml (0.02 mol) were dissolved in 60 ml of water. Myristate of 4-hydroxyphenyldimethylsulfomethyl sulfate (trade name: SANCELER My-DSP, manufactured by Sanshin Kagaku Kogyo Co., Ltd.) 9.52 g (0.02 mol) was added to the solution, and the mixture was stirred for 12 hours at room temperature. The solution reacted was adjusted to pH 2 or 3 with 1N-HCl and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and freed of solvent in vacuo. The oily residue obtained was purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel and N-myristoyl-D-serine 3.8 g was obtained.

Workup

  1. customThe solution reacted
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. customThe oily residue obtained
  5. customwas purified by column chromatography (column: 2.5×15 cm) on 50 g of silica gel

Sources & evidence

ORD record
ord-d11ba624ae4143d98f75d8bbf78dacfb
Source dataset
uspto-grants-1992_05
Patent number
US05112863

Linked notes

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