Sodium Chloride → HCID 18940489, compound

HRID 355678Notes

Reaction equation

HRID 355678 reaction equation
C(Cl)Cl.[NH2:4][CH:5]([CH:11]([OH:23])[C:12]1[S:13][C:14]([CH2:17][N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:15][CH:16]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[Na+]>C(N(CC)CC)C>[C:24]([NH:4][CH:5]([CH:11]([OH:23])[C:12]1[S:13][C:14]([CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[CH:15][CH:16]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 18940427HCID 18940427, compound

Product 1

HCID 18940489HCID 18940489, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To methylene chloride solution (5 ml) of 180 mg ethyl 2-amino-3-hydroxy-3-[5-(1-pyrrolidinyl)methyl-2-thienyl]propionate diastereomers (A form and B form) was added triethylamine (300 μl), followed by dropwise addition of 80 mg of benzoyl chloride. After 30 minutes, a saturated sodium chloride aqueous solution was added to effect separation of layers, the thus separated organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. Then, the residue was subjected to silica gel column chromatography and elution was carried out with chloroform:methanol (30:1) mixed solution to obtain 110 mg of ethyl 2-benzoylamino-3-hydroxy-3-[5-(1-pyrrolidinyl)methyl-2-thienyl]propionate (diastereomer A form and B form).

Workup

  1. customseparation of layers
  2. dry with materialthe thus separated organic layer was dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. washThen, the residue was subjected to silica gel column chromatography and elution
  5. additionmixed solution

Sources & evidence

ORD record
ord-1fbaff24b9574623aec8eddd4a61b4f9
Source dataset
uspto-grants-1998_11
Patent number
US05834460

Reaction notes

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