Potassium Hydroxide → Methyl 4-((2R)-2-{[[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl](tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)benzoate

HRID 896901Notes

Reaction equation

HRID 896901 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]3[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=3)[CH:32]=2)[O:27]1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2C(C)=CC=C2C)=[CH:16][CH:17]=1)[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NO.[OH-].[K+]>C(O)C>[NH2:18][C:15]1[N:14]=[CH:13][C:12]([C@@H:10]([OH:11])[CH2:9][N:8]([CH2:25][C@H:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:36]4[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=4)[CH:32]=3)[O:27]2)[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 22235265Hydroxylamine monohydrateHCID 59118110HCID 59118110, compound

Product 1

HCID 59118207Methyl 4-((2R)-2-{[[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl](tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)benzoateYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-{(2R)-2-[((tert-butoxycarbonyl){(2R)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]-2-hydroxyethyl}amino)methyl]-3,4-dihydro-2H-chromen-6-yl}benzoate (Example 375, 162 mg, 0.26 mmol) in ethanol (4 mL) was added hydroxylamine monohydrate (182 mg, 2.65 mmol) and 2 N aq. potassium hydroxide (0.66 mL, 1.32 mmol). The mixture was stirred at room temperature for 70 hours and then concentrated in vacuo. Flash chromatography of the residue using 10% methanol/ethyl acetate afforded 80 mg (43%) of the desired product containing trace impurities. This material was taken on without further purification. Mass spectroscopy gave m/z=534.3 [M+H]+ (calc'd exact mass for C30H35N3O6=533.3).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e60849ccdad54d3d92ecebb84396e062
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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