1,2-Dichloroethane → HCID 86746082, compound

HRID 847315Notes

Reaction equation

HRID 847315 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][C@@H:21]([CH:27]([CH3:29])[CH3:28])[CH:22]=[CH:23][C:24](O)=[O:25])[O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1[CH:33]=[CH:34][C:35]2N(O)N=[N:38][C:36]=2C=1.C(N)CCC.C(Cl)CCl>CN(C)C=O.C(Cl)Cl>[CH2:36]([NH:38][C:24](/[CH:23]=[CH:22]/[C@H:21]([CH:27]([CH3:28])[CH3:29])[CH2:20][C@@H:11]1[O:10][C:9]([CH3:31])([CH3:30])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:12]1[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:25])[CH2:35][CH2:34][CH3:33]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 54216548HCID 54216548, compound

Product 1

HCID 86746082HCID 86746082, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.55 g (1.26 mmol) of (S)-5-[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]-4-isopropyl-2-pentenoic acid, 0.22 g (1.6 mmol) of HOBT, 0.14 ml (1.4 mmol) of butylamine and 8 ml of methylene chloride is cooled to 0° and treated dropwise with a solution of 0.29 g (1.5 mmol) of EDC in 2 ml of dimethylformamide. Thereafter, the reaction mixture is stirred at 0° for 1 hour and subsequently at room temperature for 16 hours and then poured into ice-water and extracted with methylene chloride. The methylene chloride extracts are dried over potassium carbonate and evaporated under reduced pressure. Chromatography of the residue obtained on 10 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.53 g of t-butyl (4S,5S)-5-[(S,E)-4-(butylcarbamoyl)-2-isopropyl-3-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a pale yellow oil which is used directly in the next step without further purification.

Workup

  1. temperatureis cooled to 0°
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride extracts are dried over potassium carbonate
  4. customevaporated under reduced pressure
  5. customChromatography of the residue obtained on 10 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-9e1f04853fb2480eb6bd8857609a008b
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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