Hydrochloric Acid → N-(4(S)-Amino-5(S)-hydroxy-2(S)-isopropyl-6-piperidin-1-ylhexyl)-2-(3-methoxypropoxy)-benzamide dihydrochloride

HRID 507825Notes

Reaction equation

HRID 507825 reaction equation
[OH:1][C@H:2]([C@@H:10]([NH:32]C(=O)OC(C)(C)C)[CH2:11][C@H:12]([CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:13]([CH3:15])[CH3:14])[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[ClH:40]>>[ClH:40].[ClH:40].[NH2:32][C@H:10]([C@@H:2]([OH:1])[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH2:11][C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:16][NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86613449tert-Butyl (1(S)-(1(S)-hydroxy-2-piperidin-1-ylethyl)-3(S)-{[2-(3-methoxypropoxy)-benzoylamino]methyl}-4-methylpentyl)carbamate

Product 1

HCID 11466572N-(4(S)-Amino-5(S)-hydroxy-2(S)-isopropyl-6-piperidin-1-ylhexyl)-2-(3-methoxypropoxy)-benzamide dihydrochloride

Procedure

The solution of 0.024 g of tert-butyl (1(S)-(1(S)-hydroxy-2-piperidin-1-ylethyl)-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate in 1 ml of 4M HCl (in dioxane) is stirred at 0° C. over 3 hours and subsequently concentrated by evaporation to dryness—the residue is dissolved in 1 ml of tert-butanol, frozen and lyophilized under high vacuum. The title compound is obtained as a white powder. Rf=0.09 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=2.95 (gradient I).

Workup

  1. concentrationsubsequently concentrated by evaporation to dryness—the residue
  2. dissolutionis dissolved in 1 ml of tert-butanol
  3. temperaturefrozen

Sources & evidence

ORD record
ord-8e9a49eabe554d4f93e2d89d2f9d6c89
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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