Dichloromethane → HCID 69083344, compound

HRID 1396261Notes

Reaction equation

HRID 1396261 reaction equation
C(O[C:6]([N:8](C)[C:9]1[S:10][C@H:11]2[O:17][C@H:16]([CH2:18][CH2:19][C:20](OCC)=[O:21])[C@@H:15]([O:25]CC3C=CC(OC)=CC=3)[C@H:14]([O:35]CC3C=CC(OC)=CC=3)[C@H:12]2[N:13]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].ClCCl.[C:55]([OH:61])([C:57]([F:60])([F:59])[F:58])=[O:56]>C1COCC1>[F:58][C:57]([F:60])([F:59])[C:55]([OH:61])=[O:56].[OH:21][CH2:20][CH2:19][CH2:18][C@H:16]1[O:17][C@H:11]2[C@H:12]([N:13]=[C:9]([NH:8][CH3:6])[S:10]2)[C@@H:14]([OH:35])[C@@H:15]1[OH:25]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydrideHCID 69083740HCID 69083740, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.03%HCID 69083344HCID 69083344, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 77 (150 mg, 0.23 mmol) in THF (10 mL) was treated with LiAlH4 (26.6 mg, 0.70 mmol) for 3 h at room temperature. The reaction mixture was then quenched by addition of saturated aqueous NH4Cl (20 mL), extracted with dichloromethane (3×30 mL), and dried over anhydrous magnesium sulfate. The filtrate was concentrated under vacuum to give crude compound 78 as a yellow oil (90 mg), which was dissolved into dichloromethane (10 mL) and treated with TFA (1 mL) overnight at room temperature. Removal of volatiles gave a residue, which was purified by Prep-HPLC with the following conditions: [(Agilent 1200 prep HPLC: Column, Sun fire prep. C18; mobile phase, water with 0.03% trifluoroacetic acid and CH3CN (10% up to 20% in time 10); Detector, 220 nm.)] to give the title compound 79 (Example 143) as a white solid (10.8 mg, 23%). (ES, m/z) [M+H]+ 263.1; 1H NMR (300 MHz, D2O) δ 6.18-6.20 (d, J=6.3 Hz, 1H), 4.08-4.12 (m, 1H), 3.89-3.93 (m, 1H), 3.36-3.51 (m, 4H), 2.74-2.76 (m, 3H), 1.68-1.76 (m, 1H), 1.33-1.62 (m, 3H).

Workup

  1. customThe reaction mixture was then quenched by addition of saturated aqueous NH4Cl (20 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto give crude compound 78 as a yellow oil (90 mg), which
  6. customRemoval of volatiles
  7. customgave a residue, which
  8. customwas purified by Prep-HPLC with the following conditions

Sources & evidence

ORD record
ord-729268c77e284ae79f8f517fef71a509
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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