Morpholine → (2S,3R)-3-Hydroxy-2-[4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzoylamino]-butyric acid methyl ester

HRID 422971Notes

Reaction equation

HRID 422971 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17](=[O:41])[C@@H:18]([NH:22][C:23](=[O:40])[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]2[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)[C@H:19]([OH:21])[CH3:20].[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.C(Cl)Cl.CO>C1COCC1>[CH3:15][O:16][C:17](=[O:41])[C@@H:18]([NH:22][C:23](=[O:40])[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)[C@H:19]([OH:21])[CH3:20]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 59697530(2S,3R)-Methyl 2-(4-((4-formylphenyl)ethynyl)benzamido)-3-hydroxybutanoate

Product 1

HCID 59697331(2S,3R)-3-Hydroxy-2-[4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzoylamino]-butyric acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (0.670 g, 3.16 mmol) was added to a solution of benzaldehyde 3 (0.822 g, 2.25 mmol) and morpholine (260 μL, 2.97 mmol) in THF (15 mL) under N2 atmosphere and the reaction monitored by TLC (25:1 DCM/MeOH, Rf=0.2). After stirring 4 h, the reaction mixture was quenched with saturated NaHCO3 (150 mL), extracted with EtOAc (3×100 mL), dried over MgSO4, filtered and concentrated to give a yellow syrup. Purification by silica gel chromatography (35:1 DCM/MeOH) afforded 0.844 g (86% yield) of 4 as a sticky white foam.

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3 (150 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow syrup
  7. customPurification by silica gel chromatography (35:1 DCM/MeOH)

Sources & evidence

ORD record
ord-d4c77af05ac84c89b6ff06b507b167a5
Source dataset
uspto-grants-2012_01
Patent number
US08101640B2

Reaction notes

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