1,2-Dichloroethane → HCID 18783777, compound

HRID 1108661Notes

Reaction equation

HRID 1108661 reaction equation
[CH2:1](Cl)CCl.[C:5]([OH:8])(=[O:7])[CH3:6].C([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)C.[CH:20]1[CH:21]=[CH:22][C:23]2[N:28](O)N=N[C:24]=2[CH:25]=1.O.CC[N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])C>CN(C=O)C>[NH:33]1[CH2:34][CH2:36][CH:1]([C:20]2[CH:25]=[CH:24][C:23]([NH:28][C:17]([CH:14]3[CH2:13][CH2:12][N:11]([CH2:6][C:5]([OH:8])=[O:7])[CH2:16][CH2:15]3)=[O:19])=[CH:22][CH:21]=2)[CH2:39][CH2:37]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 70069904HCID 70069904, compound

Product 1

HCID 18783777HCID 18783777, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (636 mg, 3.3 mmol) was added to a solution of the compound of Example 8(b) (682 mg, 3.3 mmol), ethyl-4-carboxypiperidine acetate 14 (646 mg, 3 mmol), HOBt. H2O (446 mg, 3.3 mmol) and DIEA (1.2 mL, 6.8 mmol) in anhydrous DMF (10 mL) at RT. After stirring for 20 h, the reaction was concentrated on rotavap (high vacuum). The resulting residue was taken into EtOAc and washed successively with H2O (3×20 mL), 10% NaHCO3 (2×20 ml) and saturated NaCl. The organic extract was dried (anhydrous Na2SO4), filtered and concentrated to yield the title compound (350 m g, 32%) as a yellow solid. HPLC k' 5.3 (Ultrasphere® ODS, gradient , A:acetonitrile B:water-0. 1% trifluoroacetic acid, 5-60% acetonitrile during 20 min; UV detection at 220 nm). MS (ESI) m/e 368.2[M+H]+.

Workup

  1. customat RT
  2. concentrationthe reaction was concentrated on rotavap (high vacuum)
  3. washwashed successively with H2O (3×20 mL), 10% NaHCO3 (2×20 ml) and saturated NaCl
  4. extractionThe organic extract
  5. dry with materialwas dried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af5030aa9eef4fc1b91edd9af537a603
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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