Hydrochloric Acid → (S)-N1-(2-amino-ethyl)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-2-morpholin-4-ylsulphonylamino-succinamide hydrochloride

HRID 744901Notes

Reaction equation

HRID 744901 reaction equation
[NH2:1][C:2](=[NH:44])[N:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][NH:10][C:11]([CH2:13][C@H:14]([NH:34][S:35]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)(=[O:37])=[O:36])[C:15]([N:17]([CH:31]2[CH2:33][CH2:32]2)[CH2:18][CH2:19][NH:20]C(=O)OCC2C=CC=CC=2)=[O:16])=[O:12])[CH2:4]1.[ClH:45]>CO.[Pd]>[ClH:45].[NH2:20][CH2:19][CH2:18][N:17]([CH:31]1[CH2:33][CH2:32]1)[C:15](=[O:16])[C@@H:14]([NH:34][S:35]([N:38]1[CH2:39][CH2:40][O:41][CH2:42][CH2:43]1)(=[O:37])=[O:36])[CH2:13][C:11]([NH:10][CH2:9][C@@H:5]1[CH2:6][CH2:7][CH2:8][N:3]([C:2]([NH2:44])=[NH:1])[CH2:4]1)=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67746098benzyl 2-[[(S)-3-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl-carbamoyl]-2-morpholin-4-ylsulphonylamino-propionyl]-cyclopropyl-amino]-ethylcarbamate

Product 1

HCID 67746050(S)-N1-(2-amino-ethyl)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-2-morpholin-4-ylsulphonylamino-succinamide hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.77 g of benzyl 2-[[(S)-3-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl-carbamoyl]-2-morpholin-4-ylsulphonylamino-propionyl]-cyclopropyl-amino]-ethylcarbamate (Example 23) are dissolved in 90 ml of methanol. After the addition of 2.13 ml of 2N hydrochloric acid and 300 mg of Pd/C (10%) the mixture is hydrogenated at room temperature for 1.5 hours, the catalyst is then filtered off and the filtrate is evaporated. The residue is dispersed with ether and the white crystals are filtered off. 2.44 g of crystalline (S)-N1-(2-amino-ethyl)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-2-morpholin-4-ylsulphonylamino-succinamide hydrochloride (1:2), MS (ISP): 503.4 (M+H), are obtained.

Workup

  1. filtrationthe catalyst is then filtered off
  2. customthe filtrate is evaporated
  3. additionThe residue is dispersed with ether
  4. filtrationthe white crystals are filtered off

Sources & evidence

ORD record
ord-5a20133279b244189940c2465df5b45c
Source dataset
uspto-grants-1996_09
Patent number
US05559232

Reaction notes

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