1,2-Dichloroethane → HCID 70171956, compound

HRID 2306262Notes

Reaction equation

HRID 2306262 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[C:14]1([C:20]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:21]2[CH:25]=[C:24]([CH2:26][C:27]([O-])=[O:28])[N:23]=[CH:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Li+].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:27](=[O:28])[CH2:26][C:24]2[N:23]=[CH:22][N:21]([C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:25]=2)[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 23690736HCID 23690736, compound

Product 1

HCID 70171956HCID 70171956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine, as described above in Step B, (842 mg, 4.52 mmol), lithium [1-(triphenylmethyl)-1H-imidazol-4-yl]acetate, as described in Example 31, Step B, (1.69 g, 4.52 mmol), EDC (953 mg, 4.97 mmol), HOBT (672 mg, 4.97 mmol) and N,N-diisopropylethylamine (1.2 mL, 6.78 mmol) in DMF (10 mL) was stirred for 18 hours. The mixture was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 5% MeOH—0.1% to 0.5% NH4OH, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a gradient of CH2Cl2—1% to 5% MeOH—0.1% to 0.5% NH4OH

Sources & evidence

ORD record
ord-41e39510aa0e44a8970ef210e20850fb
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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