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Triphenylphosphine → Rac.-n-[2,6-dimethyl-4-[[[3-[[(1,1-dimethylethyl) dimethylsilyl]oxy]benzyl]amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester

HRID 1058405
Notes
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Reaction equation

HRID 1058405 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[CH:29]=[C:28]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH:35]=2)=[O:31])[CH:27]=[C:26]([CH3:48])[C:22]=1[C:23](O)=[O:24].ClN1C(=O)CCC1=O.[CH3:57][O:58][C:59](=[O:68])[CH:60]([P:62]([O:66][CH3:67])([O:64][CH3:65])=[O:63])[NH2:61].COC(=O)C(P(OC)(OC)=O)NC(OCC1C=CC=CC=1)=O>ClCCl>[CH3:57][O:58][C:59](=[O:68])[CH:60]([P:62]([O:64][CH3:65])([O:66][CH3:67])=[O:63])[NH:61][C:23](=[O:24])[C:22]1[C:21]([CH3:20])=[CH:29][C:28]([C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH:35]=2)=[O:31])=[CH:27][C:26]=1[CH3:48]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 11084793Methyl 2-amino-2-(dimethoxyphosphoryl)acetateHCID 226615542,6-Dimethyl-4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]benzoic acid

Product 1

HCID 23560782
Rac.-n-[2,6-dimethyl-4-[[[3-[[(1,1-dimethylethyl) dimethylsilyl]oxy]benzyl]amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester
Yield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (0.762 g, 2.9 mmol) was added to a suspension of 2,6-dimethyl-4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]benzoic acid (Example 111; 1 g, 2.42 mmol) in dichloromethane (12 mL) at 25° C. The mixture was cooled to 0° C. and N-chlorosuccinimide (0.387 g, 2.9 mmol) was added. After stirring 15 min at 0° C., the mixture was stirred for an additional 15 min at 25° C. and then a solution of rac.-2-(dimethoxyphosphinyl)glycine methyl ester (Example 125) freshly prepared from rac.-N-(benzyloxycarbonyl)-2-(dimethoxyphosphinyl)glycine methyl ester (1.99 g, 6 mmol) in dichloromethane (2 mL) was added in one portion. The reaction was stirred for 5 h (a precipitate formed at 2 h), then was filtered and the solids were washed with dichloromethane and discarded. The filtrate was washed with 1N hydrochloric acid solution (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL), then was dried (MgSO4) and concentrated under reduced pressure. The residue was flash chromatographed (silica gel, 10% ethyl acetate in petroleum ether) to yield rac.-N-[2,6-dimethyl-4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (1.33 g, 93% yield) as a colorless foam.

Workup

  1. stirringthe mixture was stirred for an additional 15 min at 25° C.
  2. additionwas added in one portion
  3. stirringThe reaction was stirred for 5 h (a precipitate
  4. customformed at 2 h),
  5. filtrationthen was filtered
  6. washthe solids were washed with dichloromethane
  7. washThe filtrate was washed with 1N hydrochloric acid solution (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL)
  8. dry with materialwas dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed (silica gel, 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-b69b0d92db76422b975afe4b1a0428ec
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06515124B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes