4-Methylmorpholine → HCID 135547994, compound

HRID 982871Notes

Reaction equation

HRID 982871 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[S:17][C:16]([CH3:19])([CH3:18])[CH:15]([C:20](O)=[O:21])[N:14]=[C:13]([C:23]2[C:24](=[O:31])[O:25][C:26]([CH3:30])=[CH:27][C:28]=2[OH:29])[CH2:12]1.CN1CCOCC1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:72]([O:76][C:77](=[O:81])[CH:78]([NH2:80])[CH3:79])([CH3:75])([CH3:74])[CH3:73]>CN(C=O)C>[C:72]([O:76][C:77](=[O:81])[CH:78]([NH:80][C:20]([CH:15]1[N:14]=[C:13]([C:23]2[C:24](=[O:31])[O:25][C:26]([CH3:30])=[CH:27][C:28]=2[OH:29])[CH2:12][CH:11]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[S:17][C:16]1([CH3:18])[CH3:19])=[O:21])[CH3:79])([CH3:75])([CH3:74])[CH3:73]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 4351123Tert-butyl 2-aminopropanoateHCID 135547839HCID 135547839, compound

Product 1

HCID 135547994HCID 135547994, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(2,4-Dimethoxy-phenyl)-5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2,2-dimethyl-2,3,6,7-tetrahydro-[1,4]thiazepine-3-carboxylic acid (0.03 g), prepared as in Example 2, was dissolved in DMF (2 mL) and 2-amino-propionic acid tert-butyl ester (0.012 g), N-methylmorpholine (0.2 ml) and PyBOP (0.034 g) were added to the solution at room temperature. The mixture was stirred while the progress of the reaction was followed by analytical HPLC and when complete (16 hours) the solvent was removed in vacuo. Purification of product by preparative HPLC (RPC18 column, 2-70% acetonitrile/water containing 0.1% HCl) provided 2-({1-[7-(2,4-dimethoxy-phenyl)-5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2,2-dimethyl-2,3,6,7-tetrahydro-[1,4]thiazepin-3-yl]-methanoyl }-amino)-propionic acid tert-butyl ester (18 mg) as an off-white powder. LCMS: M+ 575.0.

Workup

  1. customwas followed by analytical HPLC and when complete (16 hours)
  2. customwas removed in vacuo
  3. customPurification of product by preparative HPLC (RPC18 column, 2-70% acetonitrile/water containing 0.1% HCl)

Sources & evidence

ORD record
ord-5b00cdddca5e48769cc8148073132feb
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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