Diisopropylethylamine → HCID 178501777, compound

HRID 234131Notes

Reaction equation

HRID 234131 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.FC(F)(F)C(O)=O.[NH2:44][CH2:45][C:46]([C:48]1[CH:53]=[CH:52][C:51]([O:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])=[C:50]([O:60][CH2:61][C:62]([O:64][CH3:65])=[O:63])[CH:49]=1)=[O:47].C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([NH:44][CH2:45][C:46]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])=[C:50]([O:60][CH2:61][C:62]([O:64][CH3:65])=[O:63])[CH:49]=2)=[O:47])=[O:18])[CH2:14][CH2:15]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 131719797HCID 131719797, compoundHCID 178453624HCID 178453624, compound

Product 1

HCID 178501777HCID 178501777, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To the solution of 877 mg (3.41 mmol) of the compound prepared in (a) (3.41 mmole) in the mixture of 6.8 ml of dimethylformamide and 1.4 ml of pyridine were added 874 mg of N,N'-disuccinimidyl carbonate and a catalytic amount of 4-dimethylaminopyridine, and the resulting mixture was stirred at room temperature for 3 hours, whereafter 1.45 g of the compound prepared in (b) and 0.59 ml of N,N-diisopropylethylamine were added. The mixture was further stirred at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the resulting solid product was purified by column chromatography on silica gel. The solid product thus obtained was washed with ether to give 1.1 g of dimethyl [[4-[[[trans-4-(t-butyloxycarbonylaminomethyl)cyclohexyl]carbonylamino]acetyl]-o-phenylene]dioxy]diacetate as pale yellow crystals (yield, 59%).

Workup

  1. additionwere added
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. customthe resulting solid product was purified by column chromatography on silica gel
  4. customThe solid product thus obtained
  5. washwas washed with ether
  6. customto give

Sources & evidence

ORD record
ord-462c1188d1284c88963a6dabc3462030
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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