1,4-Dioxane hydrochloride → HCID 68607749, compound

HRID 857261Notes

Reaction equation

HRID 857261 reaction equation
[CH2:1]([C@H:8]([NH:29][C:30]([C@@H:32]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:33][CH2:34][C:35](=[O:42])[N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:31])[C@H:9]([OH:28])[CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[ClH:60]>>[ClH:60].[C:44]([NH:43][C@H:32]([CH2:33][CH2:34][C:35](=[O:42])[N:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1)[C:30]([NH:29][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([OH:28])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)=[O:31])([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:53]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86760306HCID 86760306, compound

Product 1

HCID 68607749HCID 68607749, compound

Procedure

A 50 ml round bottom flask was charged with 1-benzyl (1S)-1-[({(1S,2R)-1-benzyl-3-[(tert-butoxycarbonyl)(3-methoxybenzyl)amino]-2-hydroxypropyl}amino)carbonyl]-4-oxo-4-(1-piperidinyl)butylcarbamate (XXXVI, EXAMPLE 3, 100 mg) in dioxane/hydrochloric acid (4 N, 4 ml). The reaction is stirred 15 minutes when HPLC analysis indicates complete de-protection. The reaction mixture is concentrated under reduced pressure. The crude product is chased with acetonitrile (5 ml) then methylene chloride (5 ml). The resulting hydrochloride salt is dried under reduced pressure, to give the title compound, M+H=631.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dry with materialThe resulting hydrochloride salt is dried under reduced pressure

Sources & evidence

ORD record
ord-2e17d07d51f54cbb9bba58786c110011
Source dataset
uspto-grants-2006_12
Patent number
US07144897B2

Reaction notes

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