Triethylamine → (S)-N-[1-(amino-imino-methyl)-piperidin-3-ylmethyl]-benzamide (R)-hydroxy-phenylacetate

HRID 963847

Reaction equation

HRID 963847 reaction equation
[OH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13]1.C(N(CC)CC)C.[C:35](S(O)(=O)=O)([NH2:37])=[NH:36]>CN(C=O)C>[OH:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:37][C:35](=[NH:36])[N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9877361Methanesulfonic acid, aminoimino-HCID 70050196(R)-N-piperidin-3-ylmethyl-benzamide (R)-hydroxy-phenyl-acetate

Product 1

HCID 86748615(S)-N-[1-(amino-imino-methyl)-piperidin-3-ylmethyl]-benzamide (R)-hydroxy-phenylacetateYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bc) 19.3 g of the mandelic acid salt obtained under Bb) are suspended in 193 ml of DMF, treated with 21.7 ml of triethylamine and 7.75 g of formamidinesulfonic acid and stirred at room temperature. The reaction mixture is evaporated and the residue is chromatographed on RP-18 silica gel with a water-acetonitrile gradient. There are isolated 13.4 g of (S)-N-[1-(amino-imino-methyl)-piperidin-3-ylmethyl]-benzamide (R)-hydroxy-phenyl-acetate (1:1), MS (FAB): 218 M--(H2N--CN).

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is chromatographed on RP-18 silica gel with a water-acetonitrile gradient

Sources & evidence

ORD record
ord-bb3b2bdcc5f9428dafcd2d78f219e09f
Source dataset
uspto-grants-1998_06
Patent number
US05763604

Linked notes

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