Hydrochloric Acid → HCID 178502615, compound

HRID 2110587Notes

Reaction equation

HRID 2110587 reaction equation
CC1(C)OC([C@H]2[N:11]([O:12][CH3:13])[C@:10]3([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]4[C:19]([C:20](=[O:22])[CH:21]=[C:9]3[O:8]2)=[CH:18][CH:17]=[CH:16][CH:15]=4)CO1.[ClH:29]>O1CCCC1>[ClH:29].[OH:8][C:9]1[C@@:10]([NH:11][O:12][CH3:13])([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:22])[CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68839446HCID 68839446, compound

Product 1

HCID 178502615HCID 178502615, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 22C (60 mg, 0.15 mmol) in a 2:1 mixture of tetrahydrofuran:2N aq. HCl (0.9 mL) was stirred at rt for 3 h and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 2:1 ethyl acetate:hexanes to give the hydrochloride salt of the title compound as a colorless amorphous solid (42 mg, 87%): [α]D=+152° (c 1.4, methanol).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by column chromatography on silica gel using 2:1 ethyl acetate

Sources & evidence

ORD record
ord-c0d1efb1c14f42109c5a0275bbb6f47a
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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