Benzaldehyde → HCID 69030343, compound

HRID 1822466Notes

Reaction equation

HRID 1822466 reaction equation
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12](=[O:41])[C@@H:13]2[CH2:17][C@@H:16]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=4)[N:22]=[C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:20]=3)[CH2:15][N:14]2[C:37]([NH:39][NH2:40])=[O:38])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[CH:42](=O)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl>CO.C1COCC1>[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12](=[O:41])[C@@H:13]2[CH2:17][C@@H:16]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=4)[N:22]=[C:21]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:20]=3)[CH2:15][N:14]2[C:37]([NH:39][NH:40][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:38])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 68490104HCID 68490104, compound

Product 1

HCID 69030343HCID 69030343, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of compound 105 (0.037 mmol) in MeOH:THF (4:1) was added benzaldehyde (0.0448 mmol). The solution was stirred at RT for 18 hrs. Borane-pyridine complex (0.37 mmol) was added followed by HCl (37%, 400 μl). The solution was stirred for 1.5 hrs and then filtrated and concentrated to dryness. The crude material was dissolved in MeOH and purified by Prep LCMS which gave the title compound (0.01 mmol). Purity by HPLC>95%. M+H+650.

Workup

  1. additionBorane-pyridine complex (0.37 mmol) was added
  2. stirringThe solution was stirred for 1.5 hrs
  3. filtrationfiltrated
  4. concentrationconcentrated to dryness
  5. dissolutionThe crude material was dissolved in MeOH
  6. custompurified by Prep LCMS which

Sources & evidence

ORD record
ord-cf8f8dc9323540559efc7548173272ba
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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