1,2-Dichloroethane → HCID 57180353, compound

HRID 1197927Notes

Reaction equation

HRID 1197927 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C@@H:10]([O:19][Si:20](OC(C)(C)C)([CH3:22])[CH3:21])[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:35](Cl)CCl.C1C=C[C:42]2N(O)N=N[C:43]=2[CH:44]=1.O>C(Cl)Cl>[O:19]([C@@H:10]([CH2:11][N:12]1[CH2:13][CH2:14][CH2:15][C:16]1=[O:17])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[Si:20]([C:43]([CH3:42])([CH3:44])[CH3:35])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 57097436HCID 57097436, compound

Product 1

HCID 57180353HCID 57180353, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.6 g (1.23 mmol) of 4-[[(2S,3S)-3-(1-t-butoxyformamido)-2-(t-butoxydimethylsiloxy)-3-(cyclohexylmethyl)propyl]amino]butyric acid was dissolved in 2 ml of methylene chloride and added dropwise at -20° to a solution of 285 mg of EDC and 200 mg of HOBT in 13 ml of methylene chloride. The reaction mixture was subsequently warmed to room temperature within 15 minutes, stirred at this temperature for 17 hours and subsequently poured into water and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate, evaporated under reduced pressure and the residue was chromatographed on 10 g of silica gel using a mixture of methylene chloride and isopropanol as the eluting agent, whereby there were obtained 480 mg of t-butyl [(1S,2S)-2-(t-butyldimethylsiloxy)-1-(cyclohexylmethyl)-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate as an oil which was used directly in the next step.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customthe residue was chromatographed on 10 g of silica gel using
  5. additiona mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-38a8554eaa964671aff82ef1c240324a
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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