Diisopropylethylamine → HCID 131726116, compound

HRID 724552Notes

Reaction equation

HRID 724552 reaction equation
[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[O:63][C:64](OC2C=CC([N+]([O-])=O)=CC=2)=[O:65])[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4].[C:76]([O:80][C:81]([NH:83][CH2:84][CH2:85][OH:86])=[O:82])([CH3:79])([CH3:78])[CH3:77].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(#N)C>[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[O:63][C:64]([O:86][CH2:85][CH2:84][NH:83][C:81]([O:80][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:82])=[O:65])[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 131726117HCID 131726117, compound

Product 1

HCID 131726116HCID 131726116, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the compound of Example 5A (83 mg, 0.081 mmol), 2-(tert-butyloxycarbonylamino)ethanol (26 mg, 0.161 mmol), DMAP (10 mg) and Hunig's base (0.1 mL) in acetonitrile (1 mL) was stirred at 90° C. overnight. The reaction mixture was partitioned between H2O and EtOAc. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (45% ethyl acetate/hexane) to give the title compound (73 mg, 86% yield).

Workup

  1. customThe reaction mixture was partitioned between H2O and EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-127b3ae18f404905880ff74514c7bff8
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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