Hydrochloric Acid → HCID 68490959, compound

HRID 539141Notes

Reaction equation

HRID 539141 reaction equation
C[O:2][C:3](=[O:58])[CH2:4][NH:5][C:6](=[O:57])[C@H:7]([NH:11][C:12](=[O:56])[C@H:13]([NH:21][C:22](=[O:55])[C@H:23]([NH:25][C:26](=[O:54])[CH2:27][C@@H:28]([OH:53])/[CH:29]=[CH:30]/[CH2:31][CH2:32][S:33][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:24])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:8]([CH3:10])[CH3:9].[Li+].[OH-].C(Cl)(Cl)Cl.Cl>C1COCC1.O>[OH:53][C@@H:28](/[CH:29]=[CH:30]/[CH2:31][CH2:32][S:33][C:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:27][C:26]([NH:25][C@H:23]([CH3:24])[C:22]([NH:21][C@H:13]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:12]([NH:11][C@H:7]([CH:8]([CH3:9])[CH3:10])[C:6]([NH:5][CH2:4][C:3]([OH:58])=[O:2])=[O:57])=[O:56])=[O:55])=[O:54]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6212ChloroformHCID 68494967HCID 68494967, compound

Product 1

HCID 68490959HCID 68490959, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 13 (190 mg, 0.236 mmol) in THF (4 mL) was added a solution of LiOH (8.48 mg, 0.354 mmol) in H2O (1 mL) at 0° C. After stirring for 1 h CHCl3 (60 mL) was added to the solution followed by 1M HCl (10 mL). The layers were separated and the aqueous phase washed with CHCl3 (2×10 mL). The organic layers were combined, washed with brine, dried with MgSO4 and concentrated in vacuo. The crude material was then purified by flash column chromatography on silica gel (eluent 2% MeOH/CH2Cl2) to give 14 (80 mg, 0.1 mmol, 43%) as a pale yellow solid: Rf 0.21 AcOH/MeOH/CH2Cl2/(1:4:95).

Workup

  1. additionwas added to the solution
  2. customThe layers were separated
  3. washthe aqueous phase washed with CHCl3 (2×10 mL)
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was then purified by flash column chromatography on silica gel (eluent 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1f711616ecff40e493a34552badfa2c7
Source dataset
uspto-grants-2014_10
Patent number
US08865655B2

Reaction notes

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