1,2-Dichloroethane → HCID 70678529, compound

HRID 1689982Notes

Reaction equation

HRID 1689982 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[N:9]([C@H:12]3[O:16][C@@H:15]([CH2:17][OH:18])[CH:14]([O:19][P:20]([O:23][C@@H:24]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][C@:32]4([CH3:89])[C@@H:33]([CH2:85][C:86]([NH2:88])=[O:87])[C@H:34]5[N-:54][C:53]4=[C:52]([CH3:55])[C:50]4=[N:51][C:47]([C:48]([CH3:62])([CH3:61])[C@@H:49]4[CH2:56][CH2:57][C:58]([NH2:60])=[O:59])=[CH:46][C:44]4=[N:45][C:41]([C@:42]([CH2:69][C:70]([NH2:72])=[O:71])([CH3:68])[C@@H:43]4[CH2:63][CH2:64][C:65]([NH2:67])=[O:66])=[C:40]([CH3:73])[C:38]4=[N:39][C@:35]5([CH3:84])[C@:36]([CH2:80][C:81]([NH2:83])=[O:82])([CH3:79])[C@@H:37]4[CH2:74][CH2:75][C:76]([NH2:78])=[O:77])=[O:29])[CH3:25])([O-:22])=[O:21])[CH:13]3[OH:90])[CH:10]=[N:11][C:4]=2[CH:3]=1.O.[Co+2:92].CC([O:97]C(NCC(O)=O)=O)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN1CCCC1=O.C(OCC)(=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[N:9]([C@H:12]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([O:19][P:20]([O:23][C@@H:24]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][C@:32]4([CH3:89])[C@@H:33]([CH2:85][C:86]([NH2:88])=[O:87])[C@H:34]5[N-:54][C:53]4=[C:52]([CH3:55])[C:50]4=[N:51][C:47]([C:48]([CH3:62])([CH3:61])[C@@H:49]4[CH2:56][CH2:57][C:58]([NH2:60])=[O:59])=[CH:46][C:44]4=[N:45][C:41]([C@:42]([CH2:69][C:70]([NH2:72])=[O:71])([CH3:68])[C@@H:43]4[CH2:63][CH2:64][C:65]([NH2:67])=[O:66])=[C:40]([CH3:73])[C:38]4=[N:39][C@:35]5([CH3:84])[C@:36]([CH2:80][C:81]([NH2:83])=[O:82])([CH3:79])[C@@H:37]4[CH2:74][CH2:75][C:76]([NH2:78])=[O:77])=[O:29])[CH3:25])([O-:22])=[O:21])[C@H:13]3[OH:90])[CH:10]=[N:11][C:4]=2[CH:3]=1.[OH3+:97].[Co:92]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 131715232HCID 131715232, compound

Product 1

HCID 70678529HCID 70678529, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of B12a (1 g, 3.7 mmol), Boc-gly (966 mg, 5.5 mmol) and HOBt (596 mg, 4.4 mmol) in N-methylpyrrolidinone (5 mL) is treated with EDC (845 mg, 845 mg, 4.4 mmol) and stirred for 1 hour. The reaction is then diluted with ethyl acetate and extracted with water and saturated aqueous sodium hydrogencarbonate twice. The organics are dried over MgSO4, filtered and evaporated. The residue is treated with excess 4 M HCl in dioxane and aged for 1 hour. The mixture is slurried with ether and the solid is collected to afford B12b; ESIMS m/z for (M+H)+ C12H18BrN4O2 calcd.: 329.1. found: 329.1.

Workup

  1. extractionextracted with water and saturated aqueous sodium hydrogencarbonate twice
  2. dry with materialThe organics are dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. additionThe residue is treated with excess 4 M HCl in dioxane and aged for 1 hour
  6. customthe solid is collected

Sources & evidence

ORD record
ord-03f22af8cfc94d79bfa109898d5f90a8
Source dataset
uspto-grants-2012_04
Patent number
US08153635B2

Reaction notes

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