Hydrochloric Acid → HCID 69364744, compound

HRID 723763Notes

Reaction equation

HRID 723763 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]([NH:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][C@H:26]([CH2:28][N:29]5[CH:33]=[CH:32][N:31]=[N:30]5)[O:25][C:24]4=[O:34])=[CH:19][C:18]=3[F:35])[CH2:13]2)=[O:10])[CH2:4][O:3]1.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][C@H:26]([CH2:28][N:29]4[CH:33]=[CH:32][N:31]=[N:30]4)[O:25][C:24]3=[O:34])=[CH:19][C:18]=2[F:35])[CH2:13]1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69364716HCID 69364716, compound

Product 1

HCID 69364744HCID 69364744, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5R)-3-(4-((3R)-3-((4S)-2,2-Dimethyl-1,3-dioxolan-4-ylmethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (240 mg, 0.48 mM) in tetrahydrofuran (5 ml) was treated with hydrochloric acid (2M, 2 ml) and stirred at ambient temperature for 18 hours. Solid potassium carbonate was added to neutralise, and the mixture filtered, and the filtrate evaporated to dryness. 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 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (170 mg).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. customThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
  4. washeluting with
  5. temperaturea gradient increasing in polarity from 0 to 10% methanol in dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-c6d2ec7cf41742f8997c782e19e704d6
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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