Diisopropylethylamine → HCID 69364716, compound

HRID 723761Notes

Reaction equation

HRID 723761 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])[CH2:4]1.C(N(C(C)C)CC)(C)C.[C:36](=O)([O:46]C1C=CC([N+]([O-])=O)=CC=1)[O:37][CH2:38][C@@H:39]1[CH2:43][O:42][C:41]([CH3:45])([CH3:44])[O:40]1>O1CCCC1.ClCCl>[CH3:44][C:41]1([CH3:45])[O:40][C@H:39]([CH2:38][O:37][C:36]([NH:2][C@@H:3]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH2:18][C@H:17]([CH2:19][N:20]5[CH:24]=[CH:23][N:22]=[N:21]5)[O:16][C:15]4=[O:25])=[CH:10][C:9]=3[F:26])[CH2:4]2)=[O:46])[CH2:43][O:42]1

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 69363912HCID 69363912, compoundHCID 69364094HCID 69364094, compound

Product 1

HCID 69364716HCID 69364716, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5R)-3-(4-((3R)-3-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (400 mg, 1.05 mM) was suspended in tetrahydrofuran (10 ml) and treated with diisopropylethylamine (176 mg, 1.36 mM) and (4S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl 4-nitrophenyl carbonate (429 mg, 1.44 mM) dissolved in dichloromethane (5 ml). The mixture was stirred vigorously at ambient temperature for 18 hours, with the addition of two further portions of diisopropylethylamine (137 mg, 1.06 mM). Solvent was evaporated, the residue redissolved in ethyl acetate (20 ml), washed with water (3×20 ml), and dried (magnesium sulfate). After removal of the solvent, the residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (273 mg).

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue redissolved in ethyl acetate (20 ml)
  3. washwashed with water (3×20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customAfter removal of the solvent
  6. customthe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
  7. washeluting with
  8. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  9. customevaporated

Sources & evidence

ORD record
ord-b19d6de8bf1d47799ad7e48f9f54d2ba
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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