Hydrochloric Acid → HCID 67746223, compound

HRID 744898Notes

Reaction equation

HRID 744898 reaction equation
Cl.[NH2:2][C:3](=[NH:39])[N:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][NH:11][C:12]([CH2:14][C@H:15]([NH:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[C:16]([N:18]([CH2:22][C:23]([O:25]CC)=[O:24])[CH:19]2[CH2:21][CH2:20]2)=[O:17])=[O:13])[CH2:5]1.[OH-].[Li+].Cl>C1COCC1>[NH2:39][C:3](=[NH:2])[N:4]1[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][NH:11][C:12]([CH2:14][C@H:15]([NH:28][C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C:16]([N:18]([CH2:22][C:23]([OH:25])=[O:24])[CH:19]2[CH2:20][CH2:21]2)=[O:17])=[O:13])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86749860HCID 86749860, compound

Product 1

HCID 67746223HCID 67746223, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of ethyl [[(S)-3-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethylcarbamoyl]-2-benzyloxycarbonylamino-propionyl]-cyclopropyl-amino]-acetate hydrochloride (Example 1) are dissolved in 15 ml of THF, treated with 7.9 ml of 1N lithium hydroxide solution and stirred at room temperature for 90 minutes. Then, the solution is treated with 7.9 ml of 1N hydrochloric acid and evaporated. The residue is chromatographed on RP-18 with a water-acetonitrile gradient. 0.63 g of colourless [[(S)-3-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethylcarbamoyl]-2-benzyloxycarbonylamino-propionyl]-cyclopropylamino]-acetic acid, MS (ion spray): 503.5 (M+H)+, is obtained.

Workup

  1. customevaporated
  2. customThe residue is chromatographed on RP-18 with a water-acetonitrile gradient

Sources & evidence

ORD record
ord-1dc12cd83946450b9bae751d4db62e12
Source dataset
uspto-grants-1996_09
Patent number
US05559232

Reaction notes

Loading…