Diethyl chlorophosphate → HCID 72737700, compound

HRID 630597Notes

Reaction equation

HRID 630597 reaction equation
P([Cl:9])(OCC)(OCC)=O.[CH3:10][O:11][CH2:12][C@H:13]([NH:38][C:39]([C:41]1[S:45][C:44]([CH3:46])=[N:43][CH:42]=1)=[O:40])[C:14]([NH:16][C@@H:17]([CH2:35][O:36][CH3:37])[C:18]([NH:20][C@@H:21]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:22]([C@@:24]1([CH3:27])[CH2:26][O:25]1)=[O:23])=[O:19])=[O:15]>ClCCl.O.Cl[Ti](Cl)(Cl)Cl>[Cl:9][CH2:26][C@:24]([OH:25])([CH3:27])[C:22](=[O:23])[C@@H:21]([NH:20][C:18](=[O:19])[C@@H:17]([NH:16][C:14](=[O:15])[C@@H:13]([NH:38][C:39]([C:41]1[S:45][C:44]([CH3:46])=[N:43][CH:42]=1)=[O:40])[CH2:12][O:11][CH3:10])[CH2:35][O:36][CH3:37])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 13139Diethyl chlorophosphateHCID 25067547O-Methyl-N-((2-methylthiazol-5-yl)carbonyl)-L-seryl-O-methyl-N-((1S)-1-benzyl-2-((2R)- 2-methyloxiran-2-yl)-2-oxoethyl)-L-serinamide

Product 1

HCID 72737700HCID 72737700, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

Diethyl chlorophosphate (120 mg, 0.7 mmol) was dissolved in dichloromethane (5 mL). A solution of TiCl4 (1 mg, catalytic) in dichloromethane (2 mL) was added, followed by N—((S)-3-methoxy-1-(((S)-3-methoxy-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)-2-methylthiazole-5-carboxamide (300 mg, 0.58 mmol) in dichloromethane (10 mL). The reaction mixture was stirred 9 h at room temperature, then diluted with dichloromethane (10 mL) and water (10 mL). The organic layer was separated and washed with brine (5 mL) and dried over MgSO4. It was concentrated to dryness, and the residue purified on silica gel column (dichloromethane:methanol=100:1 to 80:1) to give product as a white solid (200 mg, yield 63%); MS for C25H33ClN4O7S m/z: 570 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (5 mL)
  3. dry with materialdried over MgSO4
  4. concentrationIt was concentrated to dryness
  5. customthe residue purified on silica gel column (dichloromethane:methanol=100:1 to 80:1)

Sources & evidence

ORD record
ord-7bbddc66e4644de9a63e4aeba6419809
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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