Hydrochloric Acid → (R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-[1,4]diazepan-5-one dihydrochloride

HRID 655565Notes

Reaction equation

HRID 655565 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:26][CH2:25][C:22]3([CH2:24][CH2:23]3)[C@H:21]([OH:27])[CH2:20]2)[CH2:10][C@H:9]1[CH3:28])=O)(C)(C)C.[ClH:29]>ClCCl.O1CCOCC1>[ClH:29].[ClH:29].[OH:27][C@@H:21]1[CH2:20][N:19]([CH2:18][CH2:17][CH2:16][N:11]2[C:12](=[O:15])[CH2:13][CH2:14][NH:8][C@H:9]([CH3:28])[CH2:10]2)[CH2:26][CH2:25][C:22]21[CH2:23][CH2:24]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67080649(R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 67080697(R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-[1,4]diazepan-5-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.500 g (1.26 mmol) of (R)-4-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (example ID) in 8 ml of dichloromethane was treated at 0° C. with 3.16 ml (12.64 mmol, 10 eq.) of 4 M hydrogen chloride solution in dioxane. The solution was stirred overnight and warmed up to room temperature. The solution was evaporated, suspended in toluene and evaporated (3 times) to give 0.610 g (quantitative, purity: 76%) of the title compound as white solid. MS: 296.3 (MH+).

Workup

  1. customThe solution was evaporated
  2. customevaporated (3 times)

Sources & evidence

ORD record
ord-c004bac4fbbb446ba67e29f5965f8dad
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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