Diisopropylethylamine → HCID 178476471, compound

HRID 278618Notes

Reaction equation

HRID 278618 reaction equation
Cl.[C:2]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=4)[CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)=[O:13])[CH2:8][CH2:7]1)(=[NH:4])[CH3:3].[C:34]([O:37][CH:38]([O:40][C:41](C1C=C([N+]([O-])=O)C=CC=1O)=[O:42])[CH3:39])(=[O:36])[CH3:35].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:34]([O:37][CH:38]([O:40][C:41]([CH2:3][C:2]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=4)[CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)=[O:13])[CH2:8][CH2:7]1)=[NH:4])=[O:42])[CH3:39])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 23447477HCID 23447477, compoundHCID 178465618HCID 178465618, compound

Product 1

HCID 178476471HCID 178476471, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(trans-4-acetimidoylaminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (100 mg), 0-(1-acetoxyethoxycarbonyl)-4-nitrophenol (63 mg) and diisopropylethylamine (72 mg) in DMF (4 ml) was stirred at 50t for 15 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate, washed with water, sodium hydrogen carbonate aqueous solution and brine, dried and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give a colorless solid of the title compound (89 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, sodium hydrogen carbonate aqueous solution and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f24fa10cb1324cc69b4d0110c5bc57e2
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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